[(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane
• CAS No.: 934356-91-9
• Molecular Formula: C₂₈H₄₂O₅Si
• Molecular Weight: 486.724

Synonyms:[(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane

Chemical Property of [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane

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Technology Process of [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane

There total 2 articles about [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane 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: 69.0%

benzyl bromide (100-39-0) + 5-O-(tert-butyldimethylsilyl)2,3-di-O-isopropylidene-D-ribitol (177493-29-7) → [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane (934356-91-9)

Guidance literature:

With sodium hydride;

DOI:10.1039/b504558d

Reference yield:

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) → [(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane (934356-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaBH₄

2: 69 percent / NaH

With sodium tetrahydroborate; sodium hydride;

DOI:10.1039/b504558d

Reference yield: 100.0%

[(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane (934356-91-9) → (R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (934356-92-0)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1039/b504558d

upstream raw materials:

benzyl bromide

5-O-(tert-butyldimethylsilyl)2,3-di-O-isopropylidene-D-ribitol

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Downstream raw materials:

(R)-2-Benzyloxy-2-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

1,4-bis-O-benzyl-2,3-O-isopropylidene-5-aldehydo-D-ribitol

(4S,5R)-4-Benzyloxymethyl-2,2-dimethyl-5-(R)-oxiranyl-[1,3]dioxolane

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