(2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 91897-30-2
• Molecular Formula: C₂₄H₃₃NO₈S₂
• Molecular Weight: 527.66
• Mol file: 91897-30-2.mol

Synonyms:(2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 9 articles about (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl 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: 73.0%

acetic anhydride (108-24-7) + 3,6-benzyloxycarbonylimino-3,6-dideoxy-D-mannose diethyl dithioacetal (91897-29-9) → (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester (91897-30-2)

Guidance literature:

In pyridine;

Reference yield:

((2R,3S,4S,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-carbamic acid benzyl ester (98237-78-6) → (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester (91897-30-2)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 36 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol / 18 h / 3192 Torr

3: CH₃COONa / ethanol / 8 h / Heating

4: NaHCO₃ / ethanol; H₂O / 2 h / ice-cooling

5: 52 percent / aq. 0.4 M HCl / 16 h / 95 - 100 °C

6: 74 percent / conc. HCl / 0.25 h

7: 73 percent / pyridine

With hydrogenchloride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium on activated charcoal; In pyridine; ethanol; water;

Reference yield:

methyl 3-benzyloxycarbonylamino-3-deoxy-6-O-tosyl-α-D-mannopyranoside (91897-27-7) → (2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester (91897-30-2)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd/C / ethanol / 18 h / 3192 Torr

2: CH₃COONa / ethanol / 8 h / Heating

3: NaHCO₃ / ethanol; H₂O / 2 h / ice-cooling

4: 52 percent / aq. 0.4 M HCl / 16 h / 95 - 100 °C

5: 74 percent / conc. HCl / 0.25 h

6: 73 percent / pyridine

With hydrogenchloride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium on activated charcoal; In pyridine; ethanol; water;

upstream raw materials:

acetic anhydride

3,6-benzyloxycarbonylimino-3,6-dideoxy-D-mannose diethyl dithioacetal

benzyl chloroformate

(1R,3S,4S,5S,8R)-3-Methoxy-2-oxa-6-aza-bicyclo[3.2.1]octane-4,8-diol

Downstream raw materials:

ethyl 4,6,7-tri-O-acetyl-5,8-benzyloxycarbonylimino-2,3,5,8-tetradeoxy-D-manno-oct-2-enonate

4,6,7-tri-O-acetyl-2,3,5,8-tetradeoxy-5,8-imino-D-manno-octono-1,5-lactam

swainsonine

2,4,5-tri-O-acetyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-aldehydo-D-mannose