(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

Base Information

• Chemical Name: (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran
• CAS No.: 313963-33-6
• Molecular Formula: C₃₁H₃₆O₃Si
• Molecular Weight: 484.711
• Mol file: 313963-33-6.mol

Synonyms:(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

Chemical Property of (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

There total 5 articles about (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran 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%

benzyl bromide (100-39-0) + (2S/R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-hydroxyprop-2-ynyl)tetrahydrofuran → (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran (313963-33-6)

Guidance literature:

(2S/R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-hydroxyprop-2-ynyl)tetrahydrofuran; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; at -72 - 20 ℃;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield: 78.0%

benzyl bromide (100-39-0) + (2S/R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-hydroxyprop-2-ynyl)tetrahydrofuran → (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran (313963-33-6) + (2R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

Guidance literature:

(2S/R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-hydroxyprop-2-ynyl)tetrahydrofuran; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; toluene; at 20 ℃; for 2h;

DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran (313963-30-3) → (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran (313963-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: Bu₃SnCl / tetrahydrofuran / 0.5 h / -78 - 20 °C

1.3: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / -10 °C

2.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With n-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1039/b316858a

upstream raw materials:

benzyl bromide

tert-butylchlorodiphenylsilane

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran

(S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol

Downstream raw materials:

(2S,5S)-2-(hydroxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-tert-butyldimethylsilyloxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16R/S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxyprop-17-ynyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane