Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Base Information

• Chemical Name: Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester
• CAS No.: 288104-43-8
• Molecular Formula: C₃₃H₃₈O₁₆S
• Molecular Weight: 722.721

Synonyms:Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property of Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

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Technology Process of Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

There total 6 articles about Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-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: 73.0%

Phthalic acid 1-((2R,4aR,6S,7S,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (288104-42-7) → Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (288104-43-8)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1039/b000771o

Reference yield:

phthalic anhydride (85-44-9) → Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (288104-43-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂

2: SOCl₂

3: Bu₂SnO / Microwave irradiation

4: 73 percent / p-TsOH

With thionyl chloride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; In dichloromethane; 1: Acylation / 2: Substitution / 3: Acylation / 4: Substitution;

DOI:10.1039/b000771o

Reference yield:

phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside (176040-66-7) → Phthalic acid 1-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester (288104-43-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂

2: SOCl₂

3: Bu₂SnO / Microwave irradiation

4: 73 percent / p-TsOH

With thionyl chloride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; In dichloromethane; 1: Acylation / 2: Substitution / 3: Acylation / 4: Substitution;

DOI:10.1039/b000771o

upstream raw materials:

Phthalic acid 1-((2R,4aR,6S,7S,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester

phthalic anhydride

phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside

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

Downstream raw materials:

methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside

C₅₅H₆₆O₂₄Si

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