(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester
CAS No.:189184-85-8
Molecular Formula:C₂₉H₃₅NO₉S
Molecular Weight:573.664
Hs Code.:

(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

Synonyms:(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

There total 8 articles about (1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic 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:

: 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

: 189184-85-8
(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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: 4 h / Ambient temperature

5: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

6: toluene / 4 h / 20 °C

7: HCl / 20 h / Ambient temperature

8: 94 percent / Py, 4-dimethylaminopyridine / 2 h / 20 °C

9: LiHMDS / tetrahydrofuran / 0.17 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; methanesulfonamide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; sodium sulfite; palladium on activated charcoal; In tetrahydrofuran; 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

: 189184-85-8
(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

8: LiHMDS / tetrahydrofuran / 0.17 h / Ambient temperature

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

Reference yield:

: (1S,2R,6S,7S,11R)-4,4-Dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-8,11-dicarboxylic acid 8-benzyl ester 11-tert-butyl ester

: 189184-85-8
(1R,2R,3R,4R,5S)-3,4-Diacetoxy-5-[(benzyloxycarbonyl-methyl-amino)-methyl]-2-(4-methoxy-phenylsulfanyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2: 4 h / Ambient temperature

3: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

4: toluene / 4 h / 20 °C

5: HCl / 20 h / Ambient temperature

6: 94 percent / Py, 4-dimethylaminopyridine / 2 h / 20 °C

7: LiHMDS / tetrahydrofuran / 0.17 h / Ambient temperature

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