methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside

Base Information

• Chemical Name: methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside
• CAS No.: 293728-88-8
• Molecular Formula: C₂₁H₂₂O₇S
• Molecular Weight: 418.467
• Mol file: 293728-88-8.mol

Synonyms:methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside

Chemical Property of methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside

There total 1 articles about methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

phenylcarbonochloridothioate (1005-56-7) + methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → methyl-4,6-O-phenylmethylene-2,3-thionocarbonyl-α-D-mannopyranoside (74984-85-3) + methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside (293728-88-8)

Guidance literature:

With pyridine; In dichloromethane; acetone; for 2h;

DOI:10.1139/v00-057

Reference yield: 68.0%

methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside (293728-88-8) → methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside (72904-78-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In toluene; for 0.666667h; Heating;

DOI:10.1139/v00-057

Reference yield:

methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside (293728-88-8) → methyl 2-O-benzoyl-3,6-dideoxy-α-D-threo-hex-5-enopyranoside (293728-92-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / AIBN; tris(trimethylsilyl)silane / toluene / 0.67 h / Heating

2: pyridine

3: 294 mg / 12 N aq. HCl / ethanol / 3 h / Heating

4: 82 percent / I₂; PPh₃; imidazole / toluene / 4 h / 55 °C

5: 52 percent / AgF; pyridine / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; iodine; silver fluoride; triphenylphosphine; In ethanol; toluene; 1: radical deoxygenation / 2: Condensation / 3: Hydrolysis / 4: Substitution / 5: Dehydroiodination;

DOI:10.1139/v00-057

upstream raw materials:

phenylcarbonochloridothioate

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside

Downstream raw materials:

methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside

methyl 2-O-benzoyl-3-deoxy-α-D-arabino-hexopyranoside

methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-arabino-3-deoxy-hexopyranoside]

methyl 2-O-benzoyl-3,6-dideoxy-α-D-threo-hex-5-enopyranoside