(8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane

Base Information

• Chemical Name: (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane
• CAS No.: 638222-20-5
• Molecular Formula: C₃₂H₅₂O₅S₂Si
• Molecular Weight: 608.979

Synonyms:(8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane

Chemical Property of (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane

There total 18 articles about (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane 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: 95.0%

t-butyldimethylsiyl triflate (69739-34-0) + (8S,10R,12S,15R)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecan-12-ol (638222-32-9) → (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane (638222-20-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/ol035848h

Reference yield:

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane (80910-01-6,108836-41-5,144069-33-0,134733-19-0) → (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane (638222-20-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-butyllithium / tetrahydrofuran; heptane / 0.25 h / 20 °C

1.2: 98 percent / tetrahydrofuran; heptane / 1 h / -10 °C

2.1: 96 percent / iodine; aqueous sodium hydrogen carbonate / acetonitrile / 1 h / 0 °C

3.1: 94 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran; methanol / -78 °C

4.1: 99 percent / para-toluenesulfonic acid monohydrate / acetone / 1 h / 0 °C

5.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 91 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 3 h / -78 - -30 °C

7.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

7.2: 93 percent / tetrahydrofuran / 3 h / -10 °C

8.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

9.1: 98 percent / sodium methoxide / methanol; CH₂Cl₂ / -10 - 5 °C

10.1: 19 percent / perchloric acid / acetonitrile; CH₂Cl₂; H₂O / 0.5 h / 0 °C

11.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; perchloric acid; oxalyl dichloride; diethyl methoxy borane; tetrabutyl ammonium fluoride; iodine; isopropylmagnesium chloride; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; acetone; acetonitrile; 6.1: Swern oxidation;

DOI:10.1021/ol035848h

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (8S,10R,12S,15R)-12-(tert-butyldimethylsilanyloxy)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecane (638222-20-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 75 percent / sodium hydride; tetra-n-butylammonium iodide / tetrahydrofuran / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; heptane / 0.25 h / 20 °C

2.2: 98 percent / tetrahydrofuran; heptane / 1 h / -10 °C

3.1: 96 percent / iodine; aqueous sodium hydrogen carbonate / acetonitrile / 1 h / 0 °C

4.1: 94 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran; methanol / -78 °C

5.1: 99 percent / para-toluenesulfonic acid monohydrate / acetone / 1 h / 0 °C

6.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: 91 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 3 h / -78 - -30 °C

8.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

8.2: 93 percent / tetrahydrofuran / 3 h / -10 °C

9.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

10.1: 98 percent / sodium methoxide / methanol; CH₂Cl₂ / -10 - 5 °C

11.1: 19 percent / perchloric acid / acetonitrile; CH₂Cl₂; H₂O / 0.5 h / 0 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; perchloric acid; oxalyl dichloride; diethyl methoxy borane; tetrabutyl ammonium fluoride; iodine; isopropylmagnesium chloride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; acetone; acetonitrile; 7.1: Swern oxidation;

DOI:10.1021/ol035848h

upstream raw materials:

t-butyldimethylsiyl triflate

(8S,10R,12S,15R)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecan-12-ol

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

p-methoxybenzyl chloride

Downstream raw materials:

(2R,6S,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecan-4-one

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