(3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol

Base Information

• Chemical Name: (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS No.: 431881-19-5
• Molecular Formula: C₂₅H₃₄O₅Si
• Molecular Weight: 442.627
• Mol file: 431881-19-5.mol

Synonyms:(3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property of (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol

There total 3 articles about (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-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:

2-Methoxypropene (116-11-0) + tert-butylchlorodiphenylsilane (58479-61-1) + 1,5-anhydro-D-mannitol (492-93-3,53319-04-3) → (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol (431881-19-5)

Guidance literature:

tert-butylchlorodiphenylsilane; 1,5-anhydro-D-mannitol; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.5h;

2-Methoxypropene; With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.7b03092

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol (431881-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 3 h / 0 °C

2: 16.9 g / CSA / dimethylformamide / 2 h

With 1H-imidazole; camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo0107610

Reference yield:

1,5-anhydro-D-mannitol (492-93-3,53319-04-3) → (3aR,6R,7R,7aS)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol (431881-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 3 h / 0 °C

2: 16.9 g / CSA / dimethylformamide / 2 h

With 1H-imidazole; camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo0107610

upstream raw materials:

tert-butylchlorodiphenylsilane

1,5-anhydro-D-mannitol

2-Methoxypropene

Downstream raw materials:

[(3aR,6R,7R,7aR)-7-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol

Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

(2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester