(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

Base Information

Chemical Name:(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside
CAS No.:1397285-40-3
Molecular Formula:C₃₆H₃₆O₈
Molecular Weight:596.677
Hs Code.:

Synonyms:(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

Chemical Property:

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Technology Process of (Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

There total 5 articles about (Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside 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:

: C₃₄H₃₅ClO₆

: 108-24-7
acetic anhydride

: 1397285-40-3
(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

: 1397285-41-4
(E)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

Guidance literature:: With potassium carbonate; In acetonitrile; at 82 ℃; for 3h; Overall yield = 72 %; Overall yield = 4.55 g;
DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

Reference yield:

: 144485-53-0
p-methoxyphenyl 2,3,4-tri-O-benzyl-6-O-triisopropylsilyl-α-D-mannoside

: 1397285-40-3
(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

: 1397285-41-4
(E)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl dichloride; triethylamine / dimethyl sulfoxide; dichloromethane / 1 h / -78 °C / Inert atmosphere

2: potassium carbonate / acetonitrile / 3 h / 82 °C

With oxalyl dichloride; potassium carbonate; triethylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile; 1: |Swern Oxidation;
DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

Reference yield:

: 1397285-38-9
p-methoxyphenyl 6-O-triisopropylsilyl-α-D-mannoside

: 1397285-40-3
(Z)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

: 1397285-41-4
(E)-p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

1.2: 20 °C

2.1: tetra-n-butylammoniumfluoride trihydrate / tetrahydrofuran / 16 h / 0 - 20 °C

3.1: oxalyl dichloride; triethylamine / dimethyl sulfoxide; dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: potassium carbonate / acetonitrile / 3 h / 82 °C

With oxalyl dichloride; sodium hydride; potassium carbonate; tetra-n-butylammoniumfluoride trihydrate; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil; 3.1: |Swern Oxidation;
DOI:10.1021/ol3024133 DOI:10.1021/ol3024133