((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol

Base Information

• Chemical Name: ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol
• CAS No.: 1345024-08-9
• Molecular Formula: C₂₃H₃₀O₃Si
• Molecular Weight: 382.575
• Mol file: 1345024-08-9.mol

Synonyms:

Chemical Property of ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol

There total 9 articles about ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol 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:

diiodomethane (75-11-6) + C22H28O3Si → ((1S,4R,5S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-10-3) + ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-08-9)

Guidance literature:

With diethylzinc; In dichloromethane; toluene; at 0 - 20 ℃; for 1h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo201716c

Reference yield:

tert-Butyl-[(R)-1-(2,3-dihydro-furan-3-yl)methoxy]-diphenyl-silane (287933-72-6) → ((1S,4R,5S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-10-3) + ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.25 h / -78 - 0 °C / Inert atmosphere

1.2: 1.25 h / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

With tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; pentane; 3.1: Simmons-Smith reaction;

DOI:10.1021/jo201716c

Reference yield:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate (1345023-89-3) → ((1S,4R,5S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-10-3) + ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 96 h / Inert atmosphere

2.1: sodium hydride / mineral oil / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

With diethylzinc; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; mineral oil; 4.1: Simmons-Smith reaction;

DOI:10.1021/jo201716c

upstream raw materials:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxytetrahydrofuran-2-carbonitrile

(R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-4,5-dihydrofuran-2-carbonitrile

diiodomethane

Downstream raw materials:

C₂₃H₂₈O₃Si

(1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid

(1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid methyl ster

benzyl ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamate