(3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 297135-64-9
• Molecular Formula: C₄₁H₇₄O₉S₂Si₂
• Molecular Weight: 831.336

Synonyms:(3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester

There total 3 articles about (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester 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: 86.0%

(5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid 2-trimethylsilanyl-ethyl ester (297135-63-8) → (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester (297135-64-9)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -20 ℃;

DOI:10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester (297135-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / toluene / Heating

2: 86 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / -20 °C

With tetramethylammonium triacetoxyborohydride; In acetic acid; toluene; acetonitrile; 1: Acylation / 2: Reduction;

DOI:10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6

Reference yield:

(6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one (297135-61-6) → (3R,5R,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-8-methyl-nonanoic acid 2-trimethylsilanyl-ethyl ester (297135-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / toluene / Heating

2: 86 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / -20 °C

With tetramethylammonium triacetoxyborohydride; In acetic acid; toluene; acetonitrile; 1: Acylation / 2: Reduction;

DOI:10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6

upstream raw materials:

(5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid 2-trimethylsilanyl-ethyl ester

2-(Trimethylsilyl)ethanol

(6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one

Downstream raw materials:

4-[6-(6-benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5,5-dimethyl-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid 2-trimethylsilanyl-ethyl ester

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