methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

Base Information

Chemical Name:methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside
CAS No.:838838-36-1
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

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Chemical Property of methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

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Technology Process of methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

There total 4 articles about methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-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: 42.0%

: 459-73-4
GlyOEt*HCl

: 838838-31-6
methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose

: 838838-36-1
methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

Guidance literature:: GlyOEt*HCl; methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose; With acetic acid; In tetrahydrofuran; at 20 ℃;

With sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2004.11.032

Reference yield: 42.0%

: 623-33-6
glycine ethyl ester hydrochloride

: 838838-31-6
methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose

: 838838-36-1
methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

Guidance literature:: With sodium cyanoborohydride; In methanol; at 0 - 20 ℃; diastereoselective reaction;
DOI:10.1016/j.tet.2009.04.011

Reference yield:

: 135700-48-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

: 838838-36-1
methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(ethoxycarbonylmethyl)-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / O₃ / CH₂Cl₂ / 1 h / 20 °C

2.1: 62 percent / polymer-bound PPh₃ / toluene / 1 h / 90 °C

3.1: AcOH / tetrahydrofuran / 20 °C

3.2: 42 percent / NaCNBH₃ / tetrahydrofuran / 2 h / 20 °C

With polymer-bound PPh₃; ozone; acetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetlet.2004.11.032