(2aR,3R,5S,5aR,6S,8aR,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

Base Information

Chemical Name:(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate
CAS No.:145745-85-3
Molecular Formula:C₃₁H₄₆O₇S₂Si
Molecular Weight:622.92
Hs Code.:

(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

Synonyms:(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

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Chemical Property of (2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

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Technology Process of (2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

There total 4 articles about (2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate 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: 82.0%

: 138175-75-4
(2aR*,3R*,5aS*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5-oxo-6-pivaloyloxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

: 145745-85-3
(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

: 138175-76-5
(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5-hydroxy-6-pivaloyloxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 1.5h;
DOI:10.1039/P19920002735

Reference yield:

: 3282-30-2
pivaloyl chloride

: 145745-85-3
(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / pyridine, DMAP / CH₂Cl₂ / 72 h / 45 °C

2: 14 percent / NaBH₄ / methanol; tetrahydrofuran / 1.5 h

With pyridine; dmap; sodium tetrahydroborate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/P19920002735

Reference yield:

: 145745-84-2
(2aR*,3R*,4aR*,7aS*,8S*,10aR*,10bR*)-methyl 3-dimethyl(phenyl)silyl-8-hydroxy-4a-methoxyperhydronaphtho<1,8-bc:5,4a-b'>difuran-10-spiro-2'-(1',3'-dithiane)-2a-carboxylate

: 145745-85-3
(2aR*,3R*,5S*,5aR*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5,6-dihydroxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 59 percent / toluene-p-sulfonic acid monohydrate / acetonitrile; H₂O / 4.75 h / 1) 53 deg C, 4.75 h, 2) room temperature, 1.5 h

2: 81 percent / pyridine, DMAP / CH₂Cl₂ / 72 h / 45 °C

3: 14 percent / NaBH₄ / methanol; tetrahydrofuran / 1.5 h

With pyridine; dmap; sodium tetrahydroborate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1039/P19920002735