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

Base Information

• Chemical Name: (3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 189184-75-6
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-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:

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) → (3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester (189184-75-6)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; 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:

(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 (189184-72-3) → (3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester (189184-75-6)

Guidance literature:

Multi-step reaction with 6 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

With hydrogenchloride; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester (189184-89-2) → (3S,4R,5S)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester (189184-75-6)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1016/S0040-4020(97)00182-8

upstream raw materials:

methanol

N-benzyloxycarbonyl-1,2-dihydropyridine

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

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

Downstream raw materials:

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

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