benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside

Base Information

• Chemical Name: benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside
• CAS No.: 106445-53-8
• Molecular Formula: C₃₈H₄₂O₇
• Molecular Weight: 610.747
• Mol file: 106445-53-8.mol

Synonyms:benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside

Chemical Property of benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside

There total 7 articles about benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside 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: 51.1%

(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde (102046-36-6) + allyl chloromethyl ether (3970-20-5) → benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside (106445-53-8) + benzyl 7-O-allyl-2,3,4-tri-O-benzyl-α-D-glycero-D-mannoheptopyranoside (106445-54-9)

Guidance literature:

With magnesium; mercury dichloride; In various solvent(s); -30 deg C, -20 deg C, 2h, RT, 18 h;

DOI:10.1016/0008-6215(86)80013-1

Reference yield:

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside (77455-30-2) → benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside (106445-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

2: trifluoroacetic acid / dioxane; methanol / Heating

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 51.1 percent / Mg, mercuric chloride / various solvent(s) / -30 deg C, -20 deg C, 2h, RT, 18 h

With sodium hydroxide; oxalyl dichloride; magnesium; dimethyl sulfoxide; trifluoroacetic acid; mercury dichloride; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/0008-6215(86)80013-1

Reference yield:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5) → benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside (106445-53-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / pyridine, 4-dimethylaminopyridine / 72 h / 40 °C

2: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

3: trifluoroacetic acid / dioxane; methanol / Heating

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

5: 51.1 percent / Mg, mercuric chloride / various solvent(s) / -30 deg C, -20 deg C, 2h, RT, 18 h

With pyridine; dmap; sodium hydroxide; oxalyl dichloride; magnesium; dimethyl sulfoxide; trifluoroacetic acid; mercury dichloride; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/0008-6215(86)80013-1

upstream raw materials:

(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde

allyl chloromethyl ether

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Downstream raw materials:

(2R,3S,4S,5S,6S)-2-((S)-2-Allyloxy-1-benzyloxy-ethyl)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran

benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

benzyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Acetic acid (3S,4S,5S,6R)-6-((S)-2-allyloxy-1-benzyloxy-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester