1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

Base Information

Chemical Name:1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose
CAS No.:860651-66-7
Molecular Formula:C₃₄H₄₀O₇Si
Molecular Weight:588.773
Hs Code.:

Synonyms:1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

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Chemical Property of 1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

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Technology Process of 1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

There total 3 articles about 1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-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: 90.0%

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

: 108-24-7
acetic anhydride

: 860651-66-7
1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

Guidance literature:: With sulfuric acid; acetic acid; at 20 ℃; for 16h;
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

: 860651-66-7
1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 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

3.1: 90 percent / AcOH; H₂SO₄ / 16 h / 20 °C

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

Reference yield:

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

: 860651-66-7
1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 97 percent / hexane; tetrahydrofuran / 3.5 h / -78 - 20 °C

2.1: 90 percent / AcOH; H₂SO₄ / 16 h / 20 °C

With n-butyllithium; sulfuric acid; acetic acid; In tetrahydrofuran; hexane; 1.2: Wittig reaction;
DOI:10.1055/s-2005-865328