2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

Base Information

• Chemical Name: 2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol
• CAS No.: 117174-48-8
• Molecular Formula: C₃₁H₄₀O₅Si
• Molecular Weight: 520.741
• Mol file: 117174-48-8.mol

Synonyms:2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

Chemical Property of 2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

There total 13 articles about 2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol 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: 98.0%

5-O-benzyl-2,3-O-isopropylidene-D-ribitol (117248-94-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol (117174-48-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2004.11.069

Reference yield: 98.0%

2-Benzyloxy-1-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (106839-88-7,117248-94-9,122088-60-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 2-Benzyloxy-1-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol (117174-48-8)

Guidance literature:

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

DOI:10.1016/S0040-4039(00)86662-9

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol (117174-48-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / 2 h / 20 °C

1.2: 96 percent / acetone / 72 h / 20 °C

2.1: 61 percent / sodium hydride / dimethylformamide / 3 h / 0 °C

3.1: 92 percent / potassium tert-butoxide / dimethylsulfoxide / 16 h / 100 °C

4.1: ozone / CH₂Cl₂ / -78 °C

4.2: 95 percent / triphenylphsphine / CH₂Cl₂ / -78 - 20 °C

5.1: 100 percent / methanol; triethylamine / 16 h / 20 °C

6.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

7.1: 98 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; sulfuric acid; potassium tert-butylate; sodium hydride; ozone; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.2: Fischer glycosidation;

DOI:10.1016/j.tetasy.2004.11.069

upstream raw materials:

2-Benzyloxy-1-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

tert-butylchlorodiphenylsilane

2,3-O-isopropylidene-D-ribonic-γ-lactone

5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Downstream raw materials:

Dithiocarbonic acid O-{2-benzyloxy-1-[(4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl} ester S-methyl ester

[(4S,5R)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Methanesulfonic acid (2S,3R)-5-benzyloxy-2,3-dihydroxy-pentyl ester

Methanesulfonic acid (4S,5R)-5-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester