2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone

Base Information

• Chemical Name: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone
• CAS No.: 244611-09-4
• Molecular Formula: C₃₆H₅₀O₅Si₂
• Molecular Weight: 618.961
• Mol file: 244611-09-4.mol

Synonyms:2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone

Chemical Property of 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone

There total 5 articles about 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone 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: 97.0%

(3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one (84911-43-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone (244611-09-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1021/jo025538x

Reference yield: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one (84911-43-3) → 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone (244611-09-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja512528p

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribono-γ-lactone (244611-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 70 °C

2: imidazole / dimethylformamide / 48 h / 20 °C

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/ol990763v

upstream raw materials:

t-butyldimethylsiyl triflate

(3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one

tert-butyldimethylsilyl chloride

trityl chloride

Downstream raw materials:

2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-D-ribitol

2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-D-ribitol