(R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol

Base Information

• Chemical Name: (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol
• CAS No.: 1354396-77-2
• Molecular Formula: C₂₄H₃₈O₃Si
• Molecular Weight: 402.649
• Mol file: 1354396-77-2.mol

Synonyms:(R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol

Chemical Property of (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol

There total 5 articles about (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-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:

1-[(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)propynone (1354396-65-8) → (S)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-76-1) + (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-77-2)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In methanol; at 0 ℃; for 0.166667h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/ol203114a

Reference yield:

tris-iso-propylsilyl acetylene (89343-06-6) + (2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde (618096-09-6) → (S)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-76-1) + (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-77-2)

Guidance literature:

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

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 1.16667h; optical yield given as %de;

DOI:10.1021/ol203114a

Reference yield:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → (S)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-76-1) + (R)-1-[(2R,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)prop-2-yn-1-ol (1354396-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Molecular sieve

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

2.2: 1.17 h / -78 - -20 °C

With n-butyllithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol203114a

upstream raw materials:

1-[(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxiranyl]-3-(triisopropylsilyl)propynone

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

tris-iso-propylsilyl acetylene

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde