3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose

Base Information

• Chemical Name: 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose
• CAS No.: 217089-45-7
• Molecular Formula: C₃₉H₄₆O₆Si
• Molecular Weight: 638.876

Synonyms:3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property of 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property:

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Technology Process of 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose

There total 8 articles about 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose 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: 68.0%

benzyl bromide (100-39-0) + 3-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose (668993-04-2) → 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose (217089-45-7)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 12h;

DOI:10.1039/b407468h

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose (217089-45-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / 12 h / 20 °C

2: 68 percent / NaH / 1,2-dimethoxy-ethane / 12 h

With pyridine; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1039/b407468h

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose (217089-45-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / 12 h / 20 °C

2: 68 percent / NaH / 1,2-dimethoxy-ethane / 12 h

With pyridine; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1039/b407468h

upstream raw materials:

benzyl bromide

(3aR,5R,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

3-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

Trifluoro-methanesulfonic acid (R)-2-benzyloxy-2-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

6-O-(3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-allofuranos-6-yl)-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

(3R,4S,5R)-4-Benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-3-hydroxy-dihydro-furan-2-one

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