3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose
• CAS No.: 410076-92-5
• Molecular Formula: C₁₈H₂₆O₁₀S₂
• Molecular Weight: 466.53
• Mol file: 410076-92-5.mol

Synonyms:3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose

Chemical Property of 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose

There total 2 articles about 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose 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%

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) + methanesulfonyl chloride (124-63-0) → 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose (410076-92-5)

Guidance literature:

With triethylamine; at 0 ℃;

DOI:10.1016/j.tetlet.2006.03.175

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose (410076-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaOH / dioxane / 4 h / 20 °C

2: 89 percent / Et₃N / 0 °C

With sodium hydroxide; triethylamine; In 1,4-dioxane;

DOI:10.1016/j.tetlet.2006.03.175

Reference yield: 76.0%

3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose (410076-92-5) → C16H20O4S (897930-31-3)

Guidance literature:

With sodium sulfide; In N,N-dimethyl-formamide; at 110 ℃; for 3h;

DOI:10.1016/j.tetlet.2006.03.175

upstream raw materials:

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

methanesulfonyl chloride

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

C₂₃H₂₇NO₄

C₁₆H₂₀O₄S

C₁₆H₂₀O₅