methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside
CAS No.:1621188-46-2
Molecular Formula:C₅₃H₇₄O₁₁Si₂
Molecular Weight:943.335
Hs Code.:

methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

There total 5 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-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: 86.0%

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 1621188-31-5
6-O-benzyl-1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-arabino-1-hexenopyranose

: 1621188-46-2
methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole; In dichloromethane; at 50 ℃; for 17h; diastereoselective reaction; Sealed tube; Inert atmosphere;
DOI:10.1002/anie.201612071

Reference yield: 76.0%

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 1621188-31-5
6-O-benzyl-1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-arabino-1-hexenopyranose

: 1621188-46-2
methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

: C₂₅H₄₄O₆Si₂

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; water; at 20 ℃; for 4h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201403543

Reference yield:

: 100-39-0
benzyl bromide

: 1621188-46-2
methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

: C₂₅H₄₄O₆Si₂

Guidance literature:: Multi-step reaction with 3 steps

1: lithium hexamethyldisilazane / N,N-dimethyl-formamide; tetrahydrofuran / 6 h / -40 - 0 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

3: toluene-4-sulfonic acid / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201403543