methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

Base Information

Chemical Name:methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate
CAS No.:1579197-75-3
Molecular Formula:C₃₃H₅₈O₇Si₂
Molecular Weight:622.99
Hs Code.:

Synonyms:methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

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Chemical Property of methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

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Technology Process of methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

There total 8 articles about methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate 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: 67.0%

: 67-71-0
dimethylsulfone

: 1579197-73-1
C₃₂H₅₆O₇Si₂

: 1579197-75-3
methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

Guidance literature:: With caesium carbonate; In acetonitrile; at 20 ℃;
DOI:10.1016/j.carres.2016.06.006

Reference yield: 67.0%

: 1579197-73-1
C₃₂H₅₆O₇Si₂

: 77-78-1
dimethyl sulfate

: 1579197-75-3
methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

: 1579197-77-5
C₃₃H₅₈O₇Si₂

Guidance literature:: With caesium carbonate; In acetonitrile; at 20 ℃; Overall yield = 83 %; Inert atmosphere;
DOI:10.1021/ja501460j

Reference yield:

: benzyl 2,3-di-O-triisopropylsilyl-α-D-arabinofuranoside

: 1579197-75-3
methyl (benzyl (Z)-2,3-di-O-triisopropylsilyl-5-O-methyl-a-D-altro-hex-4-enofuranosid)uronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 5 h / -78 °C

2.2: 20 °C

3.1: acetic anhydride / dimethyl sulfoxide / 20 °C

4.1: caesium carbonate / acetonitrile / 20 °C

With n-butyllithium; acetic anhydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.carres.2016.06.006