(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

Base Information

Chemical Name:(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate
CAS No.:243462-66-0
Molecular Formula:C₂₄H₃₈O₅S₂Si
Molecular Weight:498.78
Hs Code.:

(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

Synonyms:(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

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Chemical Property of (3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

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Technology Process of (3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

There total 2 articles about (3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate 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: 44.0%

: 75-15-0,12122-00-8
carbon disulfide

: 243462-62-6
(3aR,4R,5R,6S,6aR)-4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-ol

: 74-88-4
methyl iodide

: 243462-66-0
(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

Guidance literature:: (3aR,4R,5R,6S,6aR)-4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-ol; With sodium hydride; In diethyl ether; at 25 ℃; for 2h;

carbon disulfide; In diethyl ether; at 25 ℃; for 1h;

methyl iodide; In diethyl ether; at 25 ℃;
DOI:10.1515/znb-1999-0817

Reference yield:

: 243462-61-5
(3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol

: 243462-66-0
(3aR,4S,5R,6S,6aR)-O-[4-(Benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-5-yl]methansulfanyl methanthioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: BH₃*THF / tetrahydrofuran / 3 h / -25 °C

1.2: 61.8 percent / H₂O₂; NaOH / tetrahydrofuran; aq. methanol / 1 h / 55 °C

2.1: NaH / diethyl ether / 2 h / 25 °C

2.2: diethyl ether / 1 h / 25 °C

2.3: 44 percent / diethyl ether / 25 °C

With borane-THF; sodium hydride; In tetrahydrofuran; diethyl ether; 1.1: Addition / 1.2: Oxidation / 2.1: Metallation / 2.2: Addition / 2.3: Methylation;
DOI:10.1515/znb-1999-0817