methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside
• CAS No.: 82769-13-9
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 82769-13-9.mol

Synonyms:methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside

Chemical Property of methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside

There total 13 articles about methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-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:

methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside (82768-70-5) → methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside (82769-13-9)

Guidance literature:

rhodium on alumina; In benzene; for 3h; Yield given;

DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0) → methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside (82769-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87.5 percent / toluene

2: H₂ / Rh/Al₂O₃ / toluene

With hydrogen; Rh/Al₂O₃; In toluene;

DOI:10.1021/ja00386a076

Reference yield:

methyl 3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-05-9) → methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-heptopyranoside (82769-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

2: 87.5 percent / toluene

3: H₂ / Rh/Al₂O₃ / toluene

With hydrogen; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In dichloromethane; toluene;

DOI:10.1021/ja00386a076

upstream raw materials:

methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside

benzyl bromide

(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

Downstream raw materials:

(2S,3S,4S,5R)-3-Benzyloxy-2,4-dimethyl-heptane-1,5-diol

(3R,4S,6S)-5-Benzyloxy-4,6-dimethyl-7-trityloxy-heptan-3-ol

(4R,6S)-5-Benzyloxy-4,6-dimethyl-7-trityloxy-heptan-3-one

(2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol