(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:189184-84-7
Molecular Formula:C₂₂H₂₇NO₈
Molecular Weight:433.458
Hs Code.:

Synonyms:(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

There total 9 articles about (3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl 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: 94.0%

: 64-19-7,77671-22-8
acetic acid

: 189184-75-6
(3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

: 189184-84-7
(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

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

: 189184-84-7
(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 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: 4 h / Ambient temperature

7: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

8: toluene / 4 h / 20 °C

9: HCl / 20 h / Ambient temperature

10: 94 percent / Py, 4-dimethylaminopyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; 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; toluene;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

: 189184-72-3
(1S,4S,6R,7S,8R)-7,8-Dihydroxy-2-aza-bicyclo[2.2.2]octane-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

: 189184-84-7
(3S,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.615 g / para-toluenesulfonic acid / 12 h / Ambient temperature

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

3: 4 h / Ambient temperature

4: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

5: toluene / 4 h / 20 °C

6: HCl / 20 h / Ambient temperature

7: 94 percent / Py, 4-dimethylaminopyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4020(97)00182-8