phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside
• CAS No.: 175978-43-5
• Molecular Formula: C₃₁H₃₂O₈S
• Molecular Weight: 564.656
• Mol file: 175978-43-5.mol

Synonyms:phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside

Chemical Property of phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside

There total 8 articles about phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside 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: 50.0%

C47H50O8SSi (1276114-16-9) → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside (175978-43-5)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo400467g

Reference yield:

Benzoic acid (2S,3R,4S,5R,6S)-4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-oxo-pentanoyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (175978-42-4) → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside (175978-43-5)

Guidance literature:

With Dowex 50 (H⁺); In methanol; Ambient temperature;

DOI:10.1016/0008-6215(95)00346-0

Reference yield:

levulinic anhydride (40608-06-8) → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-1-thio-α-L-idopyranoside (175978-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h

2: Dowex 50 (H⁺) / methanol / Ambient temperature

With Dowex 50 (H⁺); triethylamine; In methanol; dichloromethane;

DOI:10.1016/0008-6215(95)00346-0

upstream raw materials:

Benzoic acid (2S,3R,4S,5R,6S)-4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-oxo-pentanoyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

levulinic anhydride

thiophenol

phenyl 3-O-benzyl-1-thio-α-L-idopyranoside

Downstream raw materials:

(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid

(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

C₅₀H₅₃NO₁₂

4-(hydroxymethyl)benzyl N-benzyl-N-[5-((3-O-benzyl-α-L-idopyranosyl)oxy)pentyl]carbamate