(8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

Base Information

• Chemical Name: (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol
• CAS No.: 868266-92-6
• Molecular Formula: C₃₃H₅₄O₆S₂Si
• Molecular Weight: 639.006

Synonyms:(8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

Chemical Property of (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

There total 6 articles about (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol 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: 94.0%

(8S,10R,12S,15S)-15-((R)-4-Hydroxy-3-methyl-2-methylene-butyl)-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol (868266-89-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol (868266-92-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1002/anie.200502008

Reference yield:

2-(1-methyl-2-triethylsilanyloxy-ethyl)-4-triethylsilanyloxy-hept-1-en-6-yne → (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol (868266-92-6)

Guidance literature:

Multi-step reaction with 5 steps

1: i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

4: aq. HClO₄ / acetonitrile; CH₂Cl₂ / 0.5 h / 20 °C

5: 94 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

With 1H-imidazole; perchloric acid; isopropylmagnesium chloride; sodium methylate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: Dess-Martin oxidation;

DOI:10.1002/anie.200502008

Reference yield:

1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-ol (868267-04-3) → (8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol (868266-92-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

3: aq. HClO₄ / acetonitrile; CH₂Cl₂ / 0.5 h / 20 °C

4: 94 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

With 1H-imidazole; perchloric acid; sodium methylate; Dess-Martin periodane; In methanol; dichloromethane; acetonitrile; 1: Dess-Martin oxidation;

DOI:10.1002/anie.200502008

upstream raw materials:

(8S,10R,12S,15S)-15-((R)-4-Hydroxy-3-methyl-2-methylene-butyl)-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

tert-butyldimethylsilyl chloride

1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-one

1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-ol

Downstream raw materials:

C₅₈H₉₆O₁₅Si₂

Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

(2S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-hydroxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

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