Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Base Information

• Chemical Name: Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester
• CAS No.: 259742-00-2
• Molecular Formula: C₄₁H₃₈O₈S
• Molecular Weight: 690.814
• Mol file: 259742-00-2.mol

Synonyms:Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property of Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

There total 1 articles about Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-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: 90.0%

phthalic anhydride (85-44-9) + phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside (210833-99-1) → Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (259742-00-2)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1055/s-1999-2997

Reference yield: 80.0%

Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 2,2,2-trichloro-ethyl ester + Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (259742-00-2) → Phthalic acid 1-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(2,2,2-trichloro-ethoxycarbonyloxy)-tetrahydro-pyran-2-ylmethyl] ester 2-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (259742-10-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1055/s-1999-2997

Reference yield:

Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (259742-00-2) → C56H56O13

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / DCC; DMAP / CH₂Cl₂

2: 94 percent / Zn-Cu; AcOH

3: PhIO; TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.17 h / -15 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; iodosylbenzene; 4 A molecular sieve; copper; acetic acid; dicyclohexyl-carbodiimide; zinc; In dichloromethane; 1: Esterification / 2: Substitution / 3: Cyclization;

DOI:10.1055/s-1999-2997

upstream raw materials:

phthalic anhydride

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

Downstream raw materials:

Phthalic acid 1-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(2,2,2-trichloro-ethoxycarbonyloxy)-tetrahydro-pyran-2-ylmethyl] ester 2-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Phthalic acid 1-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester 2-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester