methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

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Chemical Name:methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside
CAS No.:1590421-87-6
Molecular Formula:C₃₂H₃₃IO₅
Molecular Weight:624.516
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

There total 1 articles about methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-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: 90.0%

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

: 1590421-87-6
methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 75 ℃; for 0.5h;
DOI:10.1016/j.carres.2014.02.012

Reference yield: 26.0%

: 1590421-87-6
methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

: 62-50-0
Ethyl methanesulfonate

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

Guidance literature:: Ethyl methanesulfonate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.carres.2014.02.012

Reference yield:

: 1590421-87-6
methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside

: C₃₃H₄₄O₁₅S

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 - -20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 0.5 h / 20 °C

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

3.2: 1 h / -40 - -15 °C / Molecular sieve; Inert atmosphere

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

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; water; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1016/j.carres.2014.02.012