methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside

Base Information

• Chemical Name: methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside
• CAS No.: 268203-03-8
• Molecular Formula: C₂₆H₂₈O₄
• Molecular Weight: 404.506
• Mol file: 268203-03-8.mol

Synonyms:methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside

Chemical Property of methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside

There total 2 articles about methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside 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: 78.0%

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose (51885-24-6) + methyllithium (917-54-4) → methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside (268203-03-8) + methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-erythro-pentofuranoside

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield:

methyl 2-deoxy-5-O-trityl-α-D-erythro-pentofuranoside (16801-99-3) → methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside (268203-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

2: 78 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

With cerium(III) chloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Oxidation / 2: Methylation;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield: 70.0%

benzyl chloride (100-44-7) + methyl 2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside (268203-03-8) → methyl 3-O-benzyl-2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside (268203-04-9)

Guidance literature:

With potassium hydroxide; at 130 - 140 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00563-7

upstream raw materials:

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose

methyllithium

methyl 2-deoxy-5-O-trityl-α-D-erythro-pentofuranoside

Downstream raw materials:

methyl 3-O-benzyl-2-deoxy-3-C-methyl-5-O-triphenylmethyl-α-D-threo-pentofuranoside

methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside

methyl 3-O-benzyl-2-deoxy-3-C-methyl-α-D-threo-pentodialdo-1,4-furanoside

methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentofuranoside