(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

Base Information

Chemical Name:(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol
CAS No.:1354396-75-0
Molecular Formula:C₂₃H₃₆O₄Si
Molecular Weight:404.622
Hs Code.:

Synonyms:(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

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Chemical Property of (S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

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Technology Process of (S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

There total 5 articles about (S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-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:

: 1354396-64-7
1-[(2R,3R)-3-(4-methoxybenzyloxymethyl)-oxiranyl]-3-triisopropylsilyl-propynone

: 1354396-75-0
(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

: 1354396-74-9
(R)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

Guidance literature:: With C₃₈H₄₀N₂O₄RuS₂; In isopropyl alcohol; at 20 ℃; for 1.5h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol203114a

Reference yield:

: 89343-06-6
tris-iso-propylsilyl acetylene

: (2R,3R)-3-(4-methoxybenzyloxymethyl)oxirane-2-carbaldehyde

: 1354396-75-0
(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

: 1354396-74-9
(R)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

Guidance literature:: tris-iso-propylsilyl acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

(2R,3R)-3-(4-methoxybenzyloxymethyl)oxirane-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 3h;
DOI:10.1021/ol203114a

Reference yield:

: 143833-81-2
(Z)-4-(4-methoxybenzyloxy)but-2-en-1-ol

: 1354396-75-0
(S)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

: 1354396-74-9
(R)-1-[(2S,3R)-3-(4-methoxybenzyloxymethyl)oxiranyl]-3-triisopropylsilylprop-2-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -23 °C / Molecular sieve

2.1: sodium acetate; pyridinium chlorochromate / dichloromethane / Molecular sieve

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C

3.2: 3 h / -78 - -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; 1.1: Sharpless epoxidation;
DOI:10.1021/ol203114a