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

Base Information

• Chemical Name: methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside
• CAS No.: 82707-14-0
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 82707-14-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside 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: 86.0%

methyl 3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-05-9) → methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0)

Guidance literature:

With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -60 ℃; for 0.166667h;

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

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 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) NEt₃ / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1055/s-1999-3671

Reference yield:

benzyl bromide (100-39-0) → methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 20percent Pd(OH)2/C₂H₂, 2.) KH / 1.) dioxane, 2.) THF

2: 76 percent / n-Bu₄NF / tetrahydrofuran

3: 86 percent / COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

With palladium dihydroxide; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; acetylene; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00386a076

upstream raw materials:

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

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

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

methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

(S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

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

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

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