(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

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Chemical Name:(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid
CAS No.:404868-06-0
Molecular Formula:C₅₁H₇₆O₈Si
Molecular Weight:845.245
Hs Code.:

Synonyms:(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

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Chemical Property of (3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

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Technology Process of (3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

There total 8 articles about (3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid 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: 55.0%

: 628316-34-7
(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-ene-1,3-diol

: 404868-06-0
(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide;
DOI:10.1021/ja036521e

Reference yield:

: 21964-49-8
tetradeca-1,13-diene

: 404868-06-0
(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 40 percent / dibenzoylperoxide; HBr / diethyl ether; hexane / 1 h / 20 °C

2.1: Mg / tetrahydrofuran / 2 h / Heating

2.2: 64 percent / CuCl(COD) / tetrahydrofuran / 3 h / -40 - -10 °C

3.1: 88 percent / silver triflate; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1.5 h / -40 - -20 °C

4.1: NaOMe / methanol

5.1: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂

6.1: 92 percent / NaH / dimethylformamide / 3 h / 20 °C

7.1: 89 percent / DDQ; water / CH₂Cl₂ / 2 h / 20 °C

8.1: 55 percent / PDC / dimethylformamide

With dmap; dipyridinium dichromate; 2,6-di-tert-butyl-pyridine; water; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; magnesium; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dibenzoyl peroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja036521e

Reference yield:

: 74646-31-4
14-bromo-1-tetradecene

: 404868-06-0
(3R)-3-[2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]octadec-17-eneoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: Mg / tetrahydrofuran / 2 h / Heating

1.2: 64 percent / CuCl(COD) / tetrahydrofuran / 3 h / -40 - -10 °C

2.1: 88 percent / silver triflate; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1.5 h / -40 - -20 °C

3.1: NaOMe / methanol

4.1: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂

5.1: 92 percent / NaH / dimethylformamide / 3 h / 20 °C

6.1: 89 percent / DDQ; water / CH₂Cl₂ / 2 h / 20 °C

7.1: 55 percent / PDC / dimethylformamide

With dmap; dipyridinium dichromate; 2,6-di-tert-butyl-pyridine; water; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; magnesium; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja036521e