1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

Base Information

Chemical Name:1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose
CAS No.:1192260-17-5
Molecular Formula:C₃₁H₄₆O₆Si
Molecular Weight:542.788
Hs Code.:

Synonyms:1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

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Chemical Property of 1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

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Technology Process of 1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

There total 12 articles about 1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose 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: 91.0%

: 1236311-60-6
C₂₉H₄₄O₅Si

: 64-19-7,77671-22-8
acetic acid

: 1192260-17-5
1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

Guidance literature:: C₂₉H₄₄O₅Si; With Trimethyl orthoacetate; toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 0.25h; Inert atmosphere;

acetic acid; In acetonitrile; at 20 ℃; for 0.25h; Inert atmosphere;
DOI:10.1039/c2ob25222h

Reference yield:

: 1445-45-0
Trimethyl orthoacetate

: 1236311-60-6
C₂₉H₄₄O₅Si

: 1192260-17-5
1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

Guidance literature:: With toluene-4-sulfonic acid; acetic acid; In acetonitrile; at 20 ℃; for 0.416667h; regioselective reaction; Inert atmosphere;
DOI:10.1039/b907000a

Reference yield:

: C₁₄H₂₈O₄Si

: 1192260-17-5
1-O-acetyl-3,4-di-O-benzyl-6-O-thexyldimethylsilyl-5a-carba-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere

4.2: 3 h / -78 - 20 °C / Inert atmosphere

5.1: 1,2-dichloro-benzene / 2 h / 240 °C / Sealed tube

6.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 0.25 h

7.1: osmium(VIII) oxide; trimethylamine-N-oxide / water; acetone / 48 h / 20 °C

8.1: 1H-imidazole / tetrahydrofuran / 24 h / 15 - 20 °C

9.1: Trimethyl orthoacetate; toluene-4-sulfonic acid / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

9.2: 0.25 h / 20 °C / Inert atmosphere

With 1H-imidazole; Trimethyl orthoacetate; sodium tetrahydroborate; osmium(VIII) oxide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; ethyl acetate; 1,2-dichloro-benzene; acetone; acetonitrile; 4.2: Wittig reaction;
DOI:10.1039/c2ob25222h