methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside

Base Information

• Chemical Name: methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside
• CAS No.: 380883-54-5
• Molecular Formula: C₂₁H₂₃F₃O₇S
• Molecular Weight: 477.463
• Mol file: 380883-54-5.mol

Synonyms:methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside

Chemical Property of methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside

There total 5 articles about methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside 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: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + 3,5-di-O-benzyl-1-O-methyl-β-D-[2-2H1]arabinofuranose (380883-53-4) → methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside (380883-54-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/hlca.200490069

Reference yield:

1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside (55775-39-8) → methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside (380883-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMSO; oxalyl chloride / CH₂Cl₂ / 4 h / -70 °C

1.2: LiAlD₄ / diethyl ether / 0 - 20 °C

2.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dmap; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane;

DOI:10.1002/hlca.200490069

Reference yield:

methyl 3,5-di-O-benzyl-2-O-(4-methylbenzoyl)-β-D-[2-2H1]arabinofuranoside (380883-52-3) → methyl 3,5-di-O-benzyl-2-O-(trifluoromethyl)sulfonyl-β-D-[2-2H1]arabinofuranoside (380883-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NH₃ / methanol / 48 h / 20 °C

2: 90 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dmap; ammonia; In methanol; dichloromethane;

DOI:10.1002/hlca.200490069

upstream raw materials:

trifluoromethylsulfonic anhydride

3,5-di-O-benzyl-1-O-methyl-β-D-[2-2H1]arabinofuranose

1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside

methyl 3,5-di-O-benzyl-2-O-(4-methylbenzoyl)-β-D-[2-2H1]arabinofuranoside

Downstream raw materials:

3,5-di-O-benzyl-1-O-methyl-2-O-propanoyl-β-D-[2-2H1]ribofuranose

3,5-di-O-benzyl-1-O-methyl-β-D-[2-2H]ribofuranose

1-O-methyl-2,3,5-tris-O-(4-methylbenzoyl)-β-D-[2-2H1]ribofuranose

1-O-acetyl-2,3,5-tri-O-(4-toluoyl)-α/β-D-ribofuranose-2-2H1