5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

Chemical Name:5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose
CAS No.:454715-81-2
Molecular Formula:C₃₃H₄₀O₅Si
Molecular Weight:544.763
Hs Code.:

Synonyms:5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

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Chemical Property of 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

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Technology Process of 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 2 articles about 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 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: 97.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 454715-80-1
5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose

: 454715-81-2
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3.5h;
DOI:10.1055/s-2005-865328

Reference yield:

: 212970-72-4
{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

: 454715-81-2
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

2.2: 97 percent / hexane; tetrahydrofuran / 3.5 h / -78 - 20 °C

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; 2.2: Wittig reaction;
DOI:10.1055/s-2005-865328