[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

Base Information

Chemical Name:[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester
CAS No.:229962-66-7
Molecular Formula:C₂₁H₃₁NO₅
Molecular Weight:377.481
Hs Code.:

Synonyms:[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

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Chemical Property of [(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of [(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

There total 7 articles about [(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester 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: 70.0%

: 100-39-0
benzyl bromide

: 229962-65-6
(3aS,4R,5S,6R,6aR)-5-{[(tert-butoxy)carbonyl]amino}tetrahydro-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-4-ol

: 229962-66-7
[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1002/(SICI)1522-2675(19990505)82:5<760::AID-HLCA760>3.0.CO;2-S

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 229962-66-7
[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaHCO₃ / ethyl acetate; H₂O / 20 °C

2: 77 percent / hydrogen / 10 percent Pd/C / ethanol

3: 70 percent / NaH / dimethylformamide / 3 h / 20 °C

With hydrogen; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In ethanol; water; ethyl acetate; N,N-dimethyl-formamide; 1: Esterification / 2: Catalytic hydrogenation / 3: Etherification;
DOI:10.1002/(SICI)1522-2675(19990505)82:5<760::AID-HLCA760>3.0.CO;2-S

Reference yield:

: 104010-72-2
(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

: 229962-66-7
[(3aS,4R,5S,6R,6aR)-tetrahydro-4-hydroxy-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-5-yl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / H₂O₂; NaOH / methanol / 0.83 h / -40 °C

2: 91 percent / NaH / tetrahydrofuran / 1 h / 20 °C

3: 77 percent / NH₃ / ethanol / 3 h / 20 °C

4: NaHCO₃ / ethyl acetate; H₂O / 20 °C

5: 77 percent / hydrogen / 10 percent Pd/C / ethanol

6: 70 percent / NaH / dimethylformamide / 3 h / 20 °C

With sodium hydroxide; ammonia; hydrogen; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; 1: Epoxidation / 2: Condensation / 3: Ring cleavage / 4: Esterification / 5: Catalytic hydrogenation / 6: Etherification;
DOI:10.1002/(SICI)1522-2675(19990505)82:5<760::AID-HLCA760>3.0.CO;2-S