[ CAS No. 1128-23-0 ] {[proInfo.proName]}

Name: 1128-23-0|(3S,4R,5R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxydihydrofuran-2(3H)-one|98%
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Quality Control of [ 1128-23-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1128-23-0 ]

Product Details of [ 1128-23-0 ]

CAS No. :	1128-23-0	MDL No. :	MFCD00064331
Formula :	C₆H₁₀O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SXZYCXMUPBBULW-SKNVOMKLSA-N
M.W :	178.14	Pubchem ID :	439373
Synonyms :	L-Gulonolactone;L-Gulono-1,4-lactone	Chemical Name :	(3S,4R,5R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxydihydrofuran-2(3H)-one

Safety of [ 1128-23-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1128-23-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1128-23-0 ]
Downstream synthetic route of [ 1128-23-0 ]

[ 1128-23-0 ] Synthesis Path-Upstream 1~9

1
[ 50-81-7 ]
[ 1128-23-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen In water at 18℃; for 62 h;	[0163] To a solution of L-ascorbic acid (83.9 g, 0.477 mol) in water (600 mL) was added Pd/C (10percent, 8.3 g). The mixture was subjected to hydrogenation in a Parr hydrogenator at 48 psi, 18° C. for 62 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford L-gulonic y-lactone (81.0 g, 96percent) as an off-white solid, after drying at 50° C. in a vacuum oven for 18 hours: mp 182-184° C.
95%	With 5% rhodium on activated aluminium oxide; hydrogen In water at 20℃; for 1.5 h;	L-Ascorbic acid 4 (6.00 g, 34.10 mmol) was reduced by using 5 percent Rhon alumina (600 mg) in 50 mL of distilled water under 50 psi hydrogenpressure for 90 min in Parr hydrogenator at room temperature. Aftercompletion of reaction, (TLC check) reaction mixture was filtered through celite bed and washed with distilled water; the filtrate was concentrated under vacuo.Crude product was recrystallized from water to give pure 5 (5.80 g, 32.6 mmol, 95 percent) as a whitesolid. M.p. 185 °C. [α]D25 +22.5 (c 0.66, MeOH). IR (neat) νmax = 3443, 2925, 1790, 1215, 758,670 cm-1.1H NMR (400 MHz, D2O) δ = 4.67 (d, J = 4.6 Hz, 1H), 4.48 (dd, J = 4.6, 2.9 Hz, 1H),4.44 (dd, J = 8.3, 2.9 Hz, 1H), 4.03-3.96 (m, 1H), 3.73 (dd, J = 12.1, 3.4 Hz, 1H), 3.62 (dd, J =12.1, 5.6 Hz, 1H) ppm. 13C NMR (100 MHz, D2O) δ = 177.92, 81.31, 70.78, 70.05, 69.54, 61.46ppm. HRMS (ESI) m/z calcd for C6H10NaO6 [M+Na]+ 201.0370; found: 201.0372.

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2976 - 2977
[2] Patent: US2004/54172, 2004, A1,
[3] Patent: US2003/232889, 2003, A1, . Location in patent: Page/Page column 12
[4] Synlett, 2017, vol. 28, # 8, p. 970 - 972
[5] Tetrahedron Asymmetry, 1996, vol. 7, # 9, p. 2711 - 2720
[6] Chemistry - A European Journal, 2013, vol. 19, # 8, p. 2895 - 2902
[7] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 9892 - 9904
[8] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1351 - 1362
[9] Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, # 10, p. 266 - 272
[10] Organic Letters, 2010, vol. 12, # 22, p. 5226 - 5229
[11] Journal of the Chemical Society, Chemical Communications, 1988, # 18, p. 1221
[12] Synthetic Communications, 1995, vol. 25, # 20, p. 3263 - 3265
[13] Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9651 - 9668

2
[ 50-81-7 ]
[ 1128-23-0 ]

Reference： [1] Patent: US2004/6245, 2004, A1, . Location in patent: Page 42

3
[ 157663-13-3 ]
[ 1128-23-0 ]

Reference： [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1713
[2] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1365,1367

4
[ 945622-66-2 ]
[ 1128-23-0 ]

Reference： [1] Synlett, 2007, # 8, p. 1247 - 1250

5
[ 367523-78-2 ]
[ 1128-23-0 ]

Reference： [1] Synlett, 2007, # 8, p. 1247 - 1250

6
[ 389-36-6 ]
[ 1128-23-0 ]

Reference： [1] Helvetica Chimica Acta, 1938, vol. 21, p. 1210,1216

7
[ 87-73-0 ]
[ 1128-23-0 ]

Reference： [1] Helvetica Chimica Acta, 1938, vol. 21, p. 1210,1216

8
[ 526-97-6 ]
[ 1128-23-0 ]

Reference： [1] Carbohydrate Research, 2018, vol. 467, p. 14 - 22

9
[ 1128-23-0 ]
[ 609-06-3 ]

Reference： [1] Patent: US2003/97029, 2003, A1,

[ 1128-23-0 ] Synthesis Path-Downstream 1~5

1
[ 50-81-7 ]
[ 1128-23-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen In water at 50℃; for 24h;
97%	With ruthenium on aluminium oxide; hydrogen; silica gel In water at 50℃; for 6h;	1 Example 1 : L-Gulonic acid gamma lactone A solution of 23.1 g (0.13 mol) L-ascorbic acid and 0.1 g celite in 170.0 g water was hydrogenated over 3.0 g of 5 % RU/AI2O3 in a hydrogenator at 50 °C, 30-40 bar hydrogen pressure and stirred with 1300 rpm for 6 h. After steady uptake of hydrogen, the reaction was cooled down and the catalyst was removed by filtration over celite. Water was removed by lyophilisation to yield 22.66 g (97 %) of a white fluffy powder, which was pure by NMR. On recrystallization of the sample from water, crystalline material was obtained m.p.: 186.62 °C; [O]D1 9: + 55° (c= 4, H2O); 1H-NMR (400 MHz, DMSO-de): d = 3.44-3.55 (m, 2, -CH2); 3.71-3.77 (m, 1 , -CH); 4.16-4.24 (m, 2, -CH); 4.43-4.45 (q, 1 , -CH); 4.66 (t, 1 , -OH); 4.97-4.98(d, 1 , -OH); 5.33-5.34 (d, 1 , -OH); 5.78-5.80 (d, 1 , -OH).
96%	In water	71.A (R)-(+)-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-methanol Step A: To a solution of L-ascorbic acid (83.9 g, 0.477 mole) in water (600 mL) was added Pd/C (10%, 8.3 g). The mixture was subjected to hydrogenation in a Parr hydrogenator at 48 psi, 18° C. for 62 hrs. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford L-gulonic γ-lactone (81.0 g, 96%) as an off-white solid, after drying at 50° C. in a vacuum oven for 18 hrs: m.p. 182-184° C.

96%	With hydrogen In water at 18℃; for 62h;	2.A [0163] To a solution of L-ascorbic acid (83.9 g, 0.477 mol) in water (600 mL) was added Pd/C (10%, 8.3 g). The mixture was subjected to hydrogenation in a Parr hydrogenator at 48 psi, 18° C. for 62 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford L-gulonic y-lactone (81.0 g, 96%) as an off-white solid, after drying at 50° C. in a vacuum oven for 18 hours: mp 182-184° C.
95%	With 5% rhodium on activated aluminium oxide; hydrogen In water at 20℃; for 1.5h;	Synthesis of L-Gulono lactone (5) L-Ascorbic acid 4 (6.00 g, 34.10 mmol) was reduced by using 5 % Rhon alumina (600 mg) in 50 mL of distilled water under 50 psi hydrogenpressure for 90 min in Parr hydrogenator at room temperature. Aftercompletion of reaction, (TLC check) reaction mixture was filtered through celite bed and washed with distilled water; the filtrate was concentrated under vacuo.Crude product was recrystallized from water to give pure 5 (5.80 g, 32.6 mmol, 95 %) as a whitesolid. M.p. 185 °C. [α]D25 +22.5 (c 0.66, MeOH). IR (neat) νmax = 3443, 2925, 1790, 1215, 758,670 cm-1.1H NMR (400 MHz, D2O) δ = 4.67 (d, J = 4.6 Hz, 1H), 4.48 (dd, J = 4.6, 2.9 Hz, 1H),4.44 (dd, J = 8.3, 2.9 Hz, 1H), 4.03-3.96 (m, 1H), 3.73 (dd, J = 12.1, 3.4 Hz, 1H), 3.62 (dd, J =12.1, 5.6 Hz, 1H) ppm. 13C NMR (100 MHz, D2O) δ = 177.92, 81.31, 70.78, 70.05, 69.54, 61.46ppm. HRMS (ESI) m/z calcd for C6H10NaO6 [M+Na]+ 201.0370; found: 201.0372.
85%	With hydrogen In water at 50℃; for 72h;
83%	With palladium on activated charcoal; hydrogen In water at 50℃; for 72h; Autoclave;
75%	With hydrogen In water at 50℃; for 168h;
71%	With hydrogen In water at 60℃; for 48h;
63%	With hydrogen In water at 50℃; for 50h;
50%	With palladium 10% on activated carbon; hydrogen In water at 50℃; for 24h;
	With hydrogen In water Yield given;
8.0 g	With hydrogen In water for 1.5h;
	With palladium 10% on activated carbon; hydrogen In water at 50℃;

Reference： [1]Andrews; Crawford; Bacon [Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2976 - 2977]
[2]Current Patent Assignee: CLARIANT AG - WO2019/179773, 2019, A1 Location in patent: Page/Page column 14
[3]Current Patent Assignee: PFIZER INC - US2004/54172, 2004, A1
[4]Current Patent Assignee: PFIZER INC - US2003/232889, 2003, A1 Location in patent: Page/Page column 12
[5]Dhage, Ganesh R.; Thopate, Shankar R. [Synlett, 2017, vol. 28, # 8, p. 970 - 972]
[6]Czarnocki, Zbigniew; Mieczkowski, Jozef B.; Ziolkowski, Marek [Tetrahedron Asymmetry, 1996, vol. 7, # 9, p. 2711 - 2720]
[7]Archer, Robert M.; Royer, Sylvain F.; Mahy, William; Winn, Caroline L.; Danson, Michael J.; Bull, Steven D. [Chemistry - A European Journal, 2013, vol. 19, # 8, p. 2895 - 2902]
[8]Hering, Kirk W.; Karaveg, Khanita; Moremen, Kelley W.; Pearson, William H. [Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 9892 - 9904]
[9]Liu, Hui; Pinto, B. Mario [Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1351 - 1362]
[10]Vekemans, Jozef A. J. M.; Boerekamp, Jack; Godefroi, Erik F. [Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, # 10, p. 266 - 272]
[11]Gueret, Stephanie M.; Furkert, Daniel P.; Brimble, Margaret A. [Organic Letters, 2010, vol. 12, # 22, p. 5226 - 5229]
[12]Shing, Tony K. M. [Journal of the Chemical Society. Chemical communications, 1988, # 18, p. 1221]
[13]Soriano; Meserole; Mulcahy [Synthetic Communications, 1995, vol. 25, # 20, p. 3263 - 3265]
[14]Enev, Valentin S.; Felzmann, Wolfgang; Gromov, Alexey; Marchart, Stefan; Mulzer, Johann [Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9651 - 9668]

2
[ 608-66-2 ]
[ 1128-23-0 ]

Reference： [1]Synlett,1998,p. 475 - 476

3
[ 87-73-0 ]
[ 1128-23-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Eindampfen einer wss. Loesung unter vermindertem Druck 2: water; sodium-amalgam; sulfuric acid / Erwaermen des Reaktionsprodukts mit Methanol und wss. Salzsaeure

Reference： [1]Sutter; Reichstein [Helvetica Chimica Acta, 1938, vol. 21, p. 1210,1216]

4
[ 1128-23-0 ]
[ 609-06-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide;Fe2(SO4)3;	EXAMPLE 6 Decarboxylation of L-gulono-1,4-lactone to L-xylose Decarboxylation of L-gulono-1,4-lactone was performed by using hydrogen peroxide as oxidation agent. By using 2.5 mol L-gulono-1,4-lactone, 0.03 mol Fe2(SO4)3 as catalyst and 10 mol of hydrogen peroxide a yield of 0.457 g L-xylose per g starting material was obtained. The reaction time was 26 h, the pH about 6, and the reaction temperature about 65 C.

Reference： [1]Patent: US2003/97029,2003,A1

5
[ 6192-52-5 ]
[ 77-76-9 ]
[ 1128-23-0 ]
[ 56710-46-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran; N-methyl-acetamide;	Step B: L-Gulonic gamma-lactone (25.0 g, 140.3 mmol) was dissolved in mixture of tetrahydrofuran (140 mL) and dimethylformamide (200 mL). p-Toluenesulfonic acid monohydrate (2.67 g, 14.0 mmol) was added and the reaction mixture was cooled to 0-5 C. in an ice-water bath. 2,2-dimethoxypropane (22.4 mL, 182.4 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 18 hours. The mixture was neutralized with solid sodium carbonate (24.0 g), and stirred for 1 hour. The solid was filtered and washed with tetrahydrofuran. The THF was removed under vacuo, and DMF by distillation under high vacuum. The resulting orange solid was triturated with toluene (300 mL), filtered, washed with toluene (20 mL), and dried in a vacuum oven at 40 C. for 3 days, to yield 5,6-Isopropylidene-L-gulonic Acid gamma-lactone (28.9 g, 94%) as a pale orange solid: mp 155-158 C.; MS(APCI+)=219.0 (M++1).

Reference： [1]Patent: US2004/54172,2004,A1

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1128-23-0 ] {[proInfo.proName]}

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[ 1128-23-0 ] Synthesis Path-Upstream 1~9

[ 1128-23-0 ] Synthesis Path-Downstream 1~5

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