2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

Base Information

Chemical Name:2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane
CAS No.:186449-04-7
Molecular Formula:C₄₄H₇₂O₃S₄Si₂
Molecular Weight:833.489
Hs Code.:

2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

Synonyms:2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

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Chemical Property of 2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

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Technology Process of 2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

There total 19 articles about 2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane 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: 80.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 186449-20-7
(E)-(1S,2R,5R)-1-{2-[(1R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithian-2-yl}-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-en-2-ol

: 186449-04-7
2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

Guidance literature:: With 2,6-dimethylpyridine;
DOI:10.1021/ja963066w

Reference yield: 65.0%

: 186448-91-9
(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithian-2-yl}-5-[1,3]dithian-2-yl-3-methyl-hex-3-en-1-ol

: 74-88-4
methyl iodide

: 186449-04-7
2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

Guidance literature:: With 15-crown-5; sodium hydride;
DOI:10.1021/ja963066w

Reference yield:

: 82917-27-9
[2S,4R]-2,4-dimethyl-pentanedioic acid monomethyl ester

: 186449-04-7
2-[(E)-(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[1,3]dithian-2-yl-1-methoxy-3-methyl-hex-3-enyl]-2-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-[1,3]dithiane

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / BH₃*Me₂S

2: 93 percent / imidazole

3: 100 percent / DIBAL

4: 93 percent

5: 99 percent / BF₃*Et₂O

6: t-BuLi / hexamethylphosphoric acid triamide / -78 °C

7: 65 percent / NaH, 15-crown-5

With 1H-imidazole; 15-crown-5; dimethylsulfide borane complex; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/ja963066w