{(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

Base Information

• Chemical Name: {(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
• CAS No.: 273749-70-5
• Molecular Formula: C₃₈H₄₆Cl₃NO₁₃
• Molecular Weight: 831.141

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

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Technology Process of {(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

There total 3 articles about {(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 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: 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:

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate (136945-14-7) → {(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:

Multi-step reaction with 2 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

With trimethylsilyl trifluoromethanesulfonate; guanidinium nitrate; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane; 1: Condensation / 2: Deacetylation;

DOI:10.1021/ol0057075

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzyl)-β-D-glucopyranoside (156881-26-4) → {(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:

Multi-step reaction with 2 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

With trimethylsilyl trifluoromethanesulfonate; guanidinium nitrate; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane; 1: Condensation / 2: Deacetylation;

DOI:10.1021/ol0057075

upstream raw materials:

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

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-(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

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

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)

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

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