(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol
• CAS No.: 110920-92-8
• Molecular Formula: C₂₅H₃₄O₆Si
• Molecular Weight: 458.627
• Mol file: 110920-92-8.mol

Synonyms:(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

Chemical Property of (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

There total 2 articles about (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol 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: 99.7%

tert-butylchlorodiphenylsilane (58479-61-1) + 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8)

Guidance literature:

With dmap; In pyridine; for 20h; Ambient temperature;

DOI:10.1016/0008-6215(92)80042-Y

Reference yield: 93.0%

3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9) → (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8)

Guidance literature:

With phosphomolybdic acid; silica gel; In dichloromethane; at 20 ℃; for 5h; chemoselective reaction;

DOI:10.1002/ejoc.200800963

Reference yield: 94.4%

benzaldehyde (100-52-7) + (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8) → 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9)

Guidance literature:

With zinc(II) chloride; for 22h; Ambient temperature;

DOI:10.1016/0008-6215(92)80042-Y

upstream raw materials:

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-α-D-glucofuranose

3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

3,5-O-(R)-benzylidene-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-glucofuranose

3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

[(R)-2-Benzyloxy-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tert-butyl-diphenyl-silane

5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose