(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

Base Information

Chemical Name:(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione
CAS No.:1268600-51-6
Molecular Formula:C₂₅H₃₉NO₃S₂Si
Molecular Weight:493.807
Hs Code.:

Synonyms:(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

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Chemical Property of (4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

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Technology Process of (4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

There total 2 articles about (4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione 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: 96.0%

: (4S)-3-[(2R,3S)-3-hydroxy-2-[(benzyloxy)methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 69739-34-0
t-butyldimethylsiyl triflate

: 1268600-51-6
(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.833333h; Inert atmosphere;
DOI:10.1021/jo2000308

Reference yield:

: 1268600-38-9
(4S)-3-[3-(benzyloxy)propanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-51-6
(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate / dichloromethane / 3.42 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere

With 1-ethyl-piperidine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; In dichloromethane; 1.2: Mukaiyama reaction;
DOI:10.1021/jo2000308

Reference yield: 85.0%

: 1268600-51-6
(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-40-3
(2R,3S)-2-(benzyloxy)methyl-3-(tert-butyldimethylsilybutyldimethylsilyloxy)pent-4-en-al

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.216667h; Inert atmosphere;
DOI:10.1021/jo2000308