methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Base Information

• Chemical Name: methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside
• CAS No.: 273749-53-4
• Molecular Formula: C₄₅H₅₀Cl₃NO₁₃
• Molecular Weight: 919.25

Synonyms:methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Chemical Property of methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

There total 4 articles about methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-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: 76.0%

benzaldehyde dimethyl acetal (1125-88-8) + {(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester (273749-70-5) → methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-53-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 0.75h;

DOI:10.1021/ol0057075

Reference yield:

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate (136945-14-7) → methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / -30 - 20 °C

2: 95 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 0.33 h / 20 °C

3: 76 percent / p-TsOH monohydrate / acetonitrile / 0.75 h

With trimethylsilyl trifluoromethanesulfonate; guanidinium nitrate; 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Etherification;

DOI:10.1021/ol0057075

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzyl)-β-D-glucopyranoside (156881-26-4) → methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / -30 - 20 °C

2: 95 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 0.33 h / 20 °C

3: 76 percent / p-TsOH monohydrate / acetonitrile / 0.75 h

With trimethylsilyl trifluoromethanesulfonate; guanidinium nitrate; 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Etherification;

DOI:10.1021/ol0057075

upstream raw materials:

benzaldehyde dimethyl acetal

{(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Downstream raw materials:

methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-(β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-β-D-glucopyranoside

methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-(β-D-glucopyanosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside)

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