(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan

Base Information

• Chemical Name: (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan
• CAS No.: 124648-93-7
• Molecular Formula: C₃₉H₃₈O₅
• Molecular Weight: 586.728
• Mol file: 124648-93-7.mol

Synonyms:(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan

Chemical Property of (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan

There total 2 articles about (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan 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: 74.0%

benzyl chloride (100-44-7) + methyl 6-O-trityl-α,β-ribofuranoside (532401-38-0) → (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan (124648-93-7) + (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan (70797-90-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1246/cl.2003.190

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan (124648-93-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetyl chloride / 21 h / 20 °C

2: pyridine / 16 h / 70 °C

3: NaH / dimethylformamide / 14.17 h / 6 - 20 °C

With pyridine; sodium hydride; acetyl chloride; In N,N-dimethyl-formamide;

DOI:10.1021/ol062234e

Reference yield: 90.0%

(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan (124648-93-7) → methyl 2,3-di-O-benzyl-β-D-ribofuranoside (70831-62-8) + methyl 2,3-di-O-benzyl-α-D-ribofuranoside (532401-39-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃;

DOI:10.1246/cl.2003.190

upstream raw materials:

benzyl chloride

methyl 6-O-trityl-α,β-ribofuranoside

D-Ribose

Downstream raw materials:

methyl 2,3-di-O-benzyl-β-D-ribofuranoside

methyl 2,3-di-O-benzyl-α-D-ribofuranoside

methyl 2,3-Di-O-benzyl-β-D-ribo-pentodialdofuranoside

1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone