(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

Base Information

Chemical Name:(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
CAS No.:638222-32-9
Molecular Formula:C₂₆H₃₈O₅S₂
Molecular Weight:494.717
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 18 articles about (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 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: 79.0%

: 638222-21-6
1-[2-[(2R)-4-ethyl-2-(triethylsilanyloxy)pent-4-en-1-yl][1,3]dithian-2-yl]-3-[(4S,6R)-6-(p-methoxybenzyloxymethyl)-2,2-dimethyl[1,3]dioxan-4-yl]propan-2-one

: 638222-32-9
(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

: 638222-31-8
(8R,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

Guidance literature:: With perchloric acid; In dichloromethane; water; acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1021/ol035848h

Reference yield: 69.0%

: 638222-31-8
(8R,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)-15-(2-ethylprop-2-en-1-yl)-10-(p-methoxybenzyloxymethyl)-9,14-dioxa-1,5-dithiadispiro[5.1.5.3]hexadecan-12-ol

Guidance literature:: With perchloric acid; calcium perchlorate; In dichloromethane; water; acetonitrile; at 20 ℃; for 16h;
DOI:10.1021/ol035848h

Reference yield:

: 80910-01-6,108836-41-5,144069-33-0,134733-19-0
(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

: 638222-32-9
(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

Guidance literature:: Multi-step reaction with 10 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

With 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