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

Base Information

• Chemical Name: (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid
• CAS No.: 1345024-12-5
• Molecular Formula: C₂₃H₂₈O₄Si
• Molecular Weight: 396.558
• Mol file: 1345024-12-5.mol

Synonyms:

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

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]hexane-1-carboxylic acid

There total 8 articles about (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid 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:

((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol (1345024-08-9) → (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid (1345024-12-5)

Guidance literature:

((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol; With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; In chloroform; water; acetonitrile; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In chloroform; water; acetonitrile; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo201716c

Reference yield:

C23H28O3Si (1345024-14-7) → (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid (1345024-12-5)

Guidance literature:

C₂₃H₂₈O₃Si; With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; acetone; at 0 - 20 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In water; acetone; at 20 ℃; pH=2 - 3; Inert atmosphere;

DOI:10.1021/jo201716c

Reference yield:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate (1345023-89-3) → (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid (1345024-12-5)

Guidance literature:

Multi-step reaction with 5 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

5.1: sodium periodate; ruthenium trichloride; sodium hydrogencarbonate / chloroform; water; acetonitrile / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With ruthenium trichloride; sodium periodate; diethylzinc; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; chloroform; water; toluene; acetonitrile; 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

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

Downstream raw materials:

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

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

(E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxyacrylamide

1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione