methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
CAS No.:1590422-04-0
Molecular Formula:C₄₀H₅₀O₁₄S
Molecular Weight:786.895
Hs Code.:

Synonyms:methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

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Chemical Property of methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

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Technology Process of methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

There total 7 articles about methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 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: 82.0%

: 1591904-70-9
2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate

: 1590421-89-8
methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

: 1590422-04-0
methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

Guidance literature:: 2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate; methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside; In dichloromethane; at -40 ℃; for 0.333333h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 - -15 ℃; for 1h; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2014.02.012

Reference yield:

: 291314-27-7
methyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-α-D-glucopyranoside

: 1590422-04-0
methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / dichloromethane / 0.5 h / -10 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - -20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 0.5 h / 20 °C

4.1: dichloromethane / 0.33 h / -40 °C / Molecular sieve; Inert atmosphere

4.2: 1 h / -40 - -15 °C / Molecular sieve; Inert atmosphere

With pyridine; n-butyllithium; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.carres.2014.02.012

Reference yield:

: C₁₆H₂₀O₇

: 1590422-04-0
methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C

2.1: dichloromethane / 0.33 h / -40 °C / Molecular sieve; Inert atmosphere

2.2: 1 h / -40 - -15 °C / Molecular sieve; Inert atmosphere

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1016/j.carres.2014.02.012