ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

Base Information

Chemical Name:ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate
CAS No.:871110-63-3
Molecular Formula:C₂₁H₃₆O₇Si
Molecular Weight:428.598
Hs Code.:

Synonyms:ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

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Chemical Property of ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

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Technology Process of ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

There total 4 articles about ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate 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: 85.0%

: 871110-56-4
ethyl (E,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-hex-2-enoate

: 871110-63-3
ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

Guidance literature:: With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 20h;
DOI:10.1021/jo051681p

Reference yield:

: 852611-11-1
(E,4S,5S)-ethyl 4-(4-methoxyphenoxy)-5-hydroxy-hex-2-enoate

: 871110-63-3
ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / dimethylformamide / 2 h / 20 °C

2: 85 percent / K₃Fe(CN)6; K₂CO₃; CH₃SO₂NH₂ / (DHQD)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 h / 0 °C

With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless dihydroxylation;
DOI:10.1021/jo051681p

Reference yield:

: 150-76-5
4-methoxy-phenol

: 871110-63-3
ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / PPh₃; Pd₂(dba)3*CHCl₃

2: 100 percent / dimethylformamide / 2 h / 20 °C

3: 85 percent / K₃Fe(CN)6; K₂CO₃; CH₃SO₂NH₂ / (DHQD)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 h / 0 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; methanesulfonamide; potassium carbonate; triphenylphosphine; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Sharpless dihydroxylation;
DOI:10.1021/jo051681p