20746-64-9|(4aR,6S,7R,8R,8aR)-6-(Allyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol| Ambeed

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CAS No. :	20746-64-9
Formula :	C₁₆H₂₀O₆
M.W :	308.33
SMILES Code :	O[C@H]1[C@]2([H])[C@](COC(C3=CC=CC=C3)O2)([H])O[C@@H]([C@@H]1O)OCC=C
MDL No. :	N/A

Yield	Reaction Conditions	Operation in experiment
		STEP 1 : (4aR,6S,7R,8R,8aR)-6-(allyloxy)-2-phenylhexahydropyrano[3,2- d][1,3]dioxine-7,8-diol Into a 3-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed (2R,3R,4S,5R,6S)-2-(hydroxymethyl)- 6-(prop-2-en-1 -yloxy)oxane-3,4,5-triol (80 g, 363.27 mmol, 1.00 equiv), CSA (250 mg), (dimethoxymethyl)benzene (82 g, 538.80 mmol, 1.48 equiv), CHCI3 (1.2 L). The resultant suspension was placed in a preheated oil bath (bath temp. 90 C), and the distillate was collected. After approximately 15 ml was collected, the same volume of CHCb was added. This process was repeated. The reaction progress was monitored by TLC. The resulting mixture was washed with 1x500 ml of water and 1x500 ml of saturated aqueous sodium bicarbonate. The resulting mixture was washed with 1x500 ml of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was washed with PE/EA(20: 1) to yield (4aR,6S,7R,8R,8aR)-2-phenyl-6-(prop-2-en-1 -yloxy)-hexahydro-2H-pyrano[3,2- d][1,3]dioxine-7,8-diol as a white solid. 1 H NMR: (300 MHz, CDCI3): delta 7.54- 7.47(m, 2H), 7.41 -7.34(m, 3H), 5.99-5.86(m, 1H), 5.55(s, 1H), 5.34-5.21 (m, 2H), 5.09(s, 1H), 4.29-4.21 (m, 3H), 4.1 1 -4.05(m, 2H), 3.93(s, 2H), 3.74(s, 1H). LC-MS (ES, m/z): 634.2 [2M+NH4] +
	With camphorsulfonic acid; In acetonitrile; for 20h;	Small-scale synthesis: To a solution of allyl alpha-D-galactopyranoside (1.0 g, 4.51 mmol) in acetonitrile (25 ml) was added p-methoxybenzaldehyde dimethyl acetal (1.65 g, 9.08 mmol) followed by CSA (105 mg, 0.45 mmol). After 20 h, Et3N (0.1 ml) was added and the solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc three times and the combined organic extracts were washed with brine, dried with Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (40 g column, EtOAc/heptane: 0>20%>100%, Teledyne ISCO Combiflash) to yield a white solid.

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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P342	If experiencing respiratory symptoms:
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P372	Explosion risk in case of fire.
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P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 20746-64-9

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CAS No.: 20746-64-9

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