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

Base Information

• Chemical Name: methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside
• CAS No.: 82768-70-5
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 82768-70-5.mol

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

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

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-hept-6-enopyranoside

There total 12 articles about methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside 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: 87.5%

methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0) + Methylenetriphenylphosphorane (19493-09-5) → methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside (82768-70-5)

Guidance literature:

In various solvent(s); at 0 ℃; for 0.166667h;

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

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-hept-6-enopyranoside (82768-70-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 87.5 percent / toluene

With dimethyl sulfoxide; triethylamine; In dichloromethane; toluene;

DOI:10.1021/ja00386a076

Reference yield:

methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-04-8) → methyl 3-O-benzyl-2,4,6,7-tetradeoxy-2,4-di-C-methyl-α-D-gulo-hept-6-enopyranoside (82768-70-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / n-Bu₄NF / tetrahydrofuran

2: 86 percent / COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

3: 87.5 percent / toluene

With tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00386a076

upstream raw materials:

methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Methylenetriphenylphosphorane

benzyl bromide

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

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