(2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester

Base Information

• Chemical Name: (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester
• CAS No.: 440644-86-0
• Molecular Formula: C₅₆H₅₀F₅NO₁₁S
• Molecular Weight: 1040.07
• Mol file: 440644-86-0.mol

Synonyms:(2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester

Chemical Property of (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester

There total 2 articles about (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl 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: 78.0%

phosgene (75-44-5) + ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (39483-51-7,119645-03-3,128850-50-0,126461-54-9) + Nα-(fluoren-9-ylmethoxycarbonyl)-L-trans-hydroxyproline pentafluorophenyl ester (147836-79-1) → (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester (440644-86-0)

Guidance literature:

phosgene; N^α-(fluoren-9-ylmethoxycarbonyl)-L-trans-hydroxyproline pentafluorophenyl ester; With pyridine; In tetrahydrofuran; toluene; at -78 - 20 ℃;

ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside; With pyridine; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1002/1521-3773(20020402)41:7<1215::AID-ANIE1215>3.0.CO;2-V

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (39483-51-7,119645-03-3,128850-50-0,126461-54-9) + C27H17ClF5NO6 → (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester (440644-86-0)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1039/b313571c

Reference yield: 57.0%

(2S,4R)-4-((2S,3S,4aR,5R,7S,8R,8aR)-8-Hydroxy-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester + (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester (440644-86-0) → [(2S,3S,4aR,5R,7S,8R,8aS)-2,3,7-Trimethoxy-2,3-dimethyl-8-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Guidance literature:

Multistep reaction.;

DOI:10.1039/b313571c

upstream raw materials:

phosgene

ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

N^α-(fluoren-9-ylmethoxycarbonyl)-L-trans-hydroxyproline pentafluorophenyl ester