3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside

Base Information

• Chemical Name: 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside
• CAS No.: 264230-05-9
• Molecular Formula: C₃₉H₄₆O₁₂
• Molecular Weight: 706.787
• Mol file: 264230-05-9.mol

Synonyms:3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside

Chemical Property of 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside

There total 10 articles about 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside 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: 89.0%

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (2592-42-9,23202-83-7) + ethyl 3,4-di-O-acetyl-2,6-di-O-benzyl-1-thio-β-D-glucopyranoside (305839-24-1) → 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-β-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside + 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside (264230-05-9)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; toluene; at 20 ℃; for 0.25h;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

Reference yield: 81.0%

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (2592-42-9,23202-83-7) + 3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite (264230-04-8) → 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside (264230-05-9)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; zinc(II) chloride; In 1,4-dioxane; toluene; for 20h;

DOI:10.1021/jm000265o

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside (264230-05-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Bu₂SnO; Bu₄NBr; 3A molecular sieves / acetonitrile / 48 h / Heating

2: Ac₂O / dimethylsulfoxide / 18 h

3: NaBH₄ / ethanol; H₂O / 1 h

4: 81 percent / 4A molecular sieves; ZnCl₂; AgClO₄ / dioxane; toluene / 20 h

With sodium tetrahydroborate; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; silver perchlorate; acetic anhydride; di(n-butyl)tin oxide; zinc(II) chloride; In 1,4-dioxane; ethanol; water; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1021/jm000265o

upstream raw materials:

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

ethyl 3,4-di-O-acetyl-2,6-di-O-benzyl-1-thio-β-D-glucopyranoside

3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside

1-benzimidazolyl-5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose

5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)uridine

1-benzimidazolyl-2-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose