chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester
• CAS No.: 1015181-20-0
• Molecular Formula: C₅₈H₅₃ClN₂O₁₄
• Molecular Weight: 1037.52

Synonyms:chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

Chemical Property of chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

Chemical Property:

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98% ^*data from raw suppliers

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Technology Process of chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

There total 2 articles about chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl 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:

2-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (160137-77-9) → chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester (1015181-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / N-iodosuccinimide; Et₃SiOSO₂CF₃ / CH₂Cl₂ / -20 °C

2: 87 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0 °C

With N-iodo-succinimide; ammonium cerium(IV) nitrate; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.mencom.2007.01.004

Reference yield:

ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (560129-48-8) → chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester (1015181-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / N-iodosuccinimide; Et₃SiOSO₂CF₃ / CH₂Cl₂ / -20 °C

2: 87 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0 °C

With N-iodo-succinimide; ammonium cerium(IV) nitrate; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.mencom.2007.01.004

Reference yield: 71.0%

chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester (1015181-20-0) + ethyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside (146399-63-5) → C75H75ClN2O20 (1015181-29-9)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.mencom.2007.01.004

upstream raw materials:

2-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

C₇₅H₇₅ClN₂O₂₀

C₇₃H₇₄N₂O₁₉

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