(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

Base Information

Chemical Name:(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol
CAS No.:869338-41-0
Molecular Formula:C₂₂H₃₇IO₄Si
Molecular Weight:520.523
Hs Code.:

Synonyms:(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

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Chemical Property of (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

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Technology Process of (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

There total 8 articles about (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-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: 90.0%

: 869338-40-9
1-[(Z)-(2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-6-iodo-2-methyl-hex-5-enyloxymethyl]-4-methoxy-benzene

: 869338-41-0
(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

Guidance literature:: With hydrogenchloride; In ethanol; at 20 ℃; for 0.5h;
DOI:10.1021/ol051691c

Reference yield:

: 869338-51-2
(E)-(R)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid methyl ester

: 869338-41-0
(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

2: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

3: 67 percent / CuI

4: 95 percent / OsO₄; NaIO₄

5: 90 percent / aq. HCl / ethanol / 0.5 h / 20 °C

With hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; titanium(IV) isopropylate; In decane; ethanol; dichloromethane; toluene; 6: Wittig reaction;
DOI:10.1021/ol051691c

Reference yield:

: 132969-60-9
(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

: 869338-41-0
(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-2-iodo-vinyl)-5-(4-methoxy-benzyloxy)-4-methyl-pentan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / benzene / 20 h / 20 °C

2: 95 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

3: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

4: 67 percent / CuI

5: 95 percent / OsO₄; NaIO₄

6: 90 percent / aq. HCl / ethanol / 0.5 h / 20 °C

With hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; titanium(IV) isopropylate; In decane; ethanol; dichloromethane; toluene; benzene; 7: Wittig reaction;
DOI:10.1021/ol051691c