methyl [2-O-acetyl-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-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
CAS No.:1590422-06-2
Molecular Formula:C₃₃H₄₆O₁₄S
Molecular Weight:698.786
Hs Code.:

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

There total 9 articles about methyl [2-O-acetyl-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: 87.0%

: 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

: 1590422-06-2
methyl [2-O-acetyl-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 0 - 20 ℃; for 5h;
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

: 1590422-06-2
methyl [2-O-acetyl-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 5 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

5.1: trifluoroacetic acid / dichloromethane; water / 5 h / 0 - 20 °C

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

Reference yield:

: 1456718-87-8
methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

: 1590422-06-2
methyl [2-O-acetyl-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 3 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 0.5 h / 20 °C

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

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

3.1: trifluoroacetic acid / dichloromethane; water / 5 h / 0 - 20 °C

With water; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1016/j.carres.2014.02.012