phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside
CAS No.:262605-50-5
Molecular Formula:C₃₆H₃₆O₈S
Molecular Weight:628.743
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

There total 6 articles about phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside 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: 95.0%

: 262605-49-2
phenyl 2,3,4-tri-O-benzyl-6-O-(t-butyloxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

: 262605-50-5
phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(99)01053-4

Reference yield:

: 100-39-0
benzyl bromide

: 262605-50-5
phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 9.0 g / NaH / dimethylformamide / 3 h / 20 °C

2: 61 percent / aq. HCl / acetone / 24 h / 60 °C

3: 61 percent / DCC / CH₂Cl₂ / 16 h / 20 °C

4: 95 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Substitution / 3: Esterification / 4: Hydrolysis;
DOI:10.1016/S0040-4020(99)01053-4

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 262605-50-5
phenyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 7.65 g / pyridine / 24 h / 20 °C

2: 9.0 g / NaH / dimethylformamide / 3 h / 20 °C

3: 61 percent / aq. HCl / acetone / 24 h / 60 °C

4: 61 percent / DCC / CH₂Cl₂ / 16 h / 20 °C

5: 95 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With pyridine; hydrogenchloride; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone; 1: Substitution / 2: Alkylation / 3: Substitution / 4: Esterification / 5: Hydrolysis;
DOI:10.1016/S0040-4020(99)01053-4