methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 211231-29-7
• Molecular Formula: C₃₂H₃₈O₇
• Molecular Weight: 534.65
• Mol file: 211231-29-7.mol

Synonyms:methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property of methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

There total 3 articles about methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside 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: 45.0%

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) + allyl chloromethyl ether (3970-20-5) → methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-29-7)

Guidance literature:

With magnesium; In tetrahydrofuran; at 20 - 24 ℃;

DOI:10.1016/S0008-6215(98)00271-7

Reference yield: 34.5%

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) + allyl chloromethyl ether (3970-20-5) → 2-Allyloxy-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol + (R)-2-Allyloxy-1-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol + methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-29-7)

Guidance literature:

With magnesium; In tetrahydrofuran; for 14h;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) → methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2, Me₂SO / CH₂Cl₂ / 1 h / -60 °C

2: 34.5 percent / Mg / tetrahydrofuran / 14 h

With oxalyl dichloride; magnesium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0008-6215(98)00037-8

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

allyl chloromethyl ether

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

3-[(S)-2-Benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

methyl 2,3,4,6-tetra-O-benzyl-7-O-dibenzyloxyphosphoryl-L-glycero-α-D-manno-heptopyranoside

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

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