tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate

Base Information

• Chemical Name: tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate
• CAS No.: 1429183-77-6
• Molecular Formula: C₃₀H₄₃NO₆Si
• Molecular Weight: 541.76

Synonyms:tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate

Chemical Property of tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate

Chemical Property:

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Technology Process of tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate

There total 9 articles about tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate 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: 96.0%

tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate (1429183-74-3) + 2,2-dimethoxy-propane (77-76-9) → tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate (1429183-77-6)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0032-1317962

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate (1429183-77-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1H-imidazole / dichloromethane / 4 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

4: tetrahydrofuran; diethyl ether / -78 - -30 °C

5: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux; Inert atmosphere

6: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 24 h / 20 °C

7: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; osmium(VIII) oxide; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1055/s-0032-1317962

Reference yield:

(2S,3S)-2-amino-N-<(tert-butyloxy)carbonyl>-1,3-dihydroxy-1,2-O,N-isopropylidene-4-pentene (114301-34-7,114301-35-8,117487-58-8,122709-37-9,117487-60-2) → tert-butyl (3aS,4S,5S,6R,7aS)-4-(tert-butyldiphenylsilyloxy)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-5-ylcarbamate (1429183-77-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1H-imidazole / dichloromethane / 4 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

4: tetrahydrofuran; diethyl ether / -78 - -30 °C

5: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux; Inert atmosphere

6: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 24 h / 20 °C

7: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; osmium(VIII) oxide; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1055/s-0032-1317962

upstream raw materials:

tert-butyl (3R,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

(2S,3S)-2-amino-N-<(tert-butyloxy)carbonyl>-1,3-dihydroxy-1,2-O,N-isopropylidene-4-pentene

tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl (1S,2R,6R)-2-(tert-butyldiphenylsilyloxy)-6-hydroxycyclohex-3-enylcarbamate

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