3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Base Information

• Chemical Name: 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose
• CAS No.: 98855-04-0
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.494

Synonyms:3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Chemical Property of 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Chemical Property:

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Technology Process of 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

There total 2 articles about 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 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:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (98855-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / aq. sodium metaperiodate / dioxane / 2 h

2: 1.) n-BuLi / 1.) DME, 0.5 h, 2.) DME, RT, 1.5 h

With sodium periodate; n-butyllithium; In 1,4-dioxane;

DOI:10.1021/jo00224a025

Reference yield:

n-heptylidene triphenylphosphorane (55367-56-1) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (98855-04-0)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) DME, 0.5 h, 2.) DME, RT, 1.5 h;

DOI:10.1021/jo00224a025

Reference yield: 100.0%

3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (98855-04-0) → 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-α-D-xylofuranose (98779-31-8)

Guidance literature:

With hydrogen; nickel; In ethanol; under 2585.7 Torr;

DOI:10.1021/jo00224a025

upstream raw materials:

n-heptylidene triphenylphosphorane

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

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

Downstream raw materials:

3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-α-D-xylofuranose

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