Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 160140-44-3
• Molecular Formula: C₂₆H₂₅F₃O₆S₂
• Molecular Weight: 554.608
• Mol file: 160140-44-3.mol

Synonyms:Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

There total 14 articles about Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl 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:

trifluoromethylsulfonic anhydride (358-23-6) + phenyl 2,3-di-O-benzyl-1-thio-α-D-xylofuranoside (160140-43-2) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (160140-44-3)

Guidance literature:

With triethylamine; In dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)76839-0

Reference yield:

(3R,4R,5R)-4-Benzyloxy-5-hydroxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-ol → Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (160140-44-3)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 0.5 h / 25 °C

2: tetrabutylammonium iodide, NaH / tetrahydrofuran / 2 h / 25 °C

3: (n-Bu₄)NF / tetrahydrofuran / 0.5 h / 25 °C

4: triethylamine / CH₂Cl₂ / 0.08 h / -78 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.67.3057

Reference yield:

phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside (160140-48-7) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (160140-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammonium iodide, NaH / tetrahydrofuran / 2 h / 25 °C

2: (n-Bu₄)NF / tetrahydrofuran / 0.5 h / 25 °C

3: triethylamine / CH₂Cl₂ / 0.08 h / -78 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.67.3057

upstream raw materials:

trifluoromethylsulfonic anhydride

phenyl 2,3-di-O-benzyl-1-thio-α-D-xylofuranoside

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

benzyl bromide

Downstream raw materials:

(2R,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-(tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester

(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.0^3,7]tetradecane-6-carboxylic acid benzyl ester