(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

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Chemical Name:(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester
CAS No.:189184-81-4
Molecular Formula:C₁₄H₂₅NO₄
Molecular Weight:271.357
Hs Code.:

Synonyms:(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

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Chemical Property of (3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

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Technology Process of (3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

There total 7 articles about (3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic 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: 81.0%

: 189184-74-5
(3aS,7S,7aR)-7-Dimethylaminomethyl-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid tert-butyl ester

: 189184-81-4
(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In tert-butyl alcohol; at 60 ℃; for 20h;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

: 79328-85-1
N-benzyloxycarbonyl-1,2-dihydropyridine

: 189184-81-4
(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 43 percent / propylene oxide, trifluoroacetic anhydride / CH₂Cl₂ / 3 h / -78 °C

3: 1.) OsO₄, N-methylmorpholine N-oxide, methanesulfonamide, 2.) sodium sulfite / 1.) acetone, t-butanol, 20 deg C, 4 h, 2.) H₂O, 30 min

4: 1.615 g / para-toluenesulfonic acid / 12 h / Ambient temperature

5: 1.) H₂, 2.) H₂ / 1.) 10percent Pd/C / 1.) MeOH, 20 deg C, 2 h, 2.) H₂O, 2 h.

6: 3 h / 20 °C

7: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

8: 81 percent / para-toluenesulfonic acid / 2-methyl-propan-2-ol / 20 h / 60 °C

With osmium(VIII) oxide; methanesulfonamide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic anhydride; methyloxirane; sodium sulfite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

: 189184-89-2
(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

: 189184-81-4
(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) OsO₄, N-methylmorpholine N-oxide, methanesulfonamide, 2.) sodium sulfite / 1.) acetone, t-butanol, 20 deg C, 4 h, 2.) H₂O, 30 min

2: 1.615 g / para-toluenesulfonic acid / 12 h / Ambient temperature

3: 1.) H₂, 2.) H₂ / 1.) 10percent Pd/C / 1.) MeOH, 20 deg C, 2 h, 2.) H₂O, 2 h.

4: 3 h / 20 °C

5: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

6: 81 percent / para-toluenesulfonic acid / 2-methyl-propan-2-ol / 20 h / 60 °C

With osmium(VIII) oxide; methanesulfonamide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; sodium sulfite; palladium on activated charcoal; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1016/S0040-4020(97)00182-8