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

Base Information

• Chemical Name: (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran
• CAS No.: 313963-30-3
• Molecular Formula: C₂₄H₃₀O₃Si
• Molecular Weight: 394.586
• Mol file: 313963-30-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)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:

tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane (106731-74-2,119944-29-5,107033-46-5) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran (313963-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuLi₂Cl₄ / tetrahydrofuran / 0.25 h / -30 °C

1.2: O₃; NaHCO₃ / CH₂Cl₂ / 0.33 h / -78 °C

1.3: PPh₃ / 28 h / -78 - 20 °C

2.1: 91 percent / Amberlyst A-15 (R) / benzene / 0.25 h / Heating

With dilithium tetrachlorocuprate; Amberlyst A-15; In tetrahydrofuran; benzene;

DOI:10.1039/b316858a

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran (313963-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

2.1: CuLi₂Cl₄ / tetrahydrofuran / 0.25 h / -30 °C

2.2: O₃; NaHCO₃ / CH₂Cl₂ / 0.33 h / -78 °C

2.3: PPh₃ / 28 h / -78 - 20 °C

3.1: 91 percent / Amberlyst A-15 (R) / benzene / 0.25 h / Heating

With dmap; dilithium tetrachlorocuprate; Amberlyst A-15; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1039/b316858a

Reference yield:

(S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol (313963-29-0) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)-2-(prop-2-yne-1-oxy)tetrahydrofuran (313963-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃; NaHCO₃ / CH₂Cl₂ / 0.33 h / -78 °C

1.2: 93 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

2.1: 91 percent / Amberlyst A-15 / benzene / 0.25 h / 80 °C

With Amberlyst A-15; sodium hydrogencarbonate; ozone; In dichloromethane; benzene;

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

upstream raw materials:

tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

(2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran

[(2S,5R)-5-(3-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-methanol

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

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