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

Base Information

• Chemical Name: methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside
• CAS No.: 273749-52-3
• Molecular Formula: C₄₄H₅₂Cl₃NO₁₆
• Molecular Weight: 957.253
• Mol file: 273749-52-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(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: 87.0%

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate (136945-14-7) + methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzyl)-β-D-glucopyranoside (156881-26-4) → methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-52-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -30 - 20 ℃; for 4h;

DOI:10.1021/ol0057075

Reference yield: 95.0%

methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-52-3) → {(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)

Guidance literature:

With guanidinium nitrate; sodium methylate; In methanol; dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ol0057075

Reference yield:

methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (273749-52-3) → acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-{7-amino-6-[4,5-bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 0.33 h / 20 °C

2: 76 percent / p-TsOH monohydrate / acetonitrile / 0.75 h

3: 84 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 12.5 h / -30 - 20 °C

4: Cd / dimethylformamide; acetic acid / 12 h / 20 °C

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

DOI:10.1021/ol0057075

upstream raw materials:

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:

{(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

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

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