(4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one
• CAS No.: 861222-42-6
• Molecular Formula: C₂₇H₃₀O₃Si
• Molecular Weight: 430.619
• Mol file: 861222-42-6.mol

Synonyms:(4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one

Chemical Property of (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one

There total 9 articles about (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one 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: 67.0%

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) + phenyllithium (591-51-5) → (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one (861222-42-6)

Guidance literature:

phenyllithium; With copper(l) iodide; In diethyl ether; at -20 ℃; for 0.5h; Inert atmosphere;

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone; With chloro-trimethyl-silane; In diethyl ether; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/ejoc.201000587

Reference yield: 63.0%

(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester (861222-41-5) → (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one (861222-42-6)

Guidance literature:

(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester; With dimethylboron bromide; In dichloromethane;

In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.05.006

Reference yield:

2-O-Benzyl-3-O-(tert-butyldiphenylsilyl)glyceraldehyde (122598-86-1,145842-05-3,135840-22-1) → (4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one (861222-42-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2.08 g / methanol / 10 h / 0 - 20 °C

2.1: Mg / tetrahydrofuran / Heating

2.2: CuI / tetrahydrofuran / 0.67 h / -78 °C

2.3: Me₃SiCl / tetrahydrofuran / -78 - 20 °C

3.1: 67 percent / H₂ / Pd/C / dioxane; H₂O / 72 h / atmospheric pressure

With hydrogen; magnesium; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jo052383v

upstream raw materials:

(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate

methyl (2Z,4S)-4-benzyloxy-5-(tert-butyldiphenylsilanyloxy)-2-pentenoate

Downstream raw materials:

(4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one