5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol

Base Information

• Chemical Name: 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol
• CAS No.: 104331-69-3
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655

Synonyms:5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol

Chemical Property of 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol

Chemical Property:

Purity/Quality:

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Technology Process of 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol

There total 18 articles about 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol 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: 94.0%

vinyl magnesium bromide (1826-67-1) + 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropylidene-keto-D-erythro-2-pentulose (105544-87-4) → 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol (104331-69-3) + 5-O-(t-butyldiphenylsilyl)1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-aribitol (104331-69-3)

Guidance literature:

In tetrahydrofuran; for 2h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)84382-8

Reference yield: 94.0%

vinyl magnesium bromide (1826-67-1) + 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropylidene-keto-D-erythro-2-pentulose (105544-87-4) → 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol (104331-69-3) + 5-O-(t-butyldiphenylsilyl)1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-aribitol (104331-69-3)

Guidance literature:

In tetrahydrofuran; for 2h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)84382-8

Reference yield: 85.0%

Vinyl bromide (593-60-2,25951-54-6) + 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropylidene-keto-D-erythro-2-pentulose (105544-87-4) → 5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-ribitol (104331-69-3) + 5-O-(t-butyldiphenylsilyl)1-deoxy-3,4-O-isopropyldene-2-C-vinyl-D-aribitol (104331-69-3)

Guidance literature:

With magnesium; In tetrahydrofuran; for 3h; Yields of byproduct given; Ambient temperature;

DOI:10.1246/bcsj.62.2618

upstream raw materials:

vinyl magnesium bromide

5-O-(t-butyldiphenylsilyl)-1-deoxy-3,4-O-isopropylidene-keto-D-erythro-2-pentulose

Vinyl bromide

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(4S,5R)-(-)-5-ethyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid

(S)-2-[(4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-propionaldehyde

1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-ethanol

5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose

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