acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 219703-42-1
• Molecular Formula: C₆₈H₇₁NO₁₈
• Molecular Weight: 1190.31

Synonyms:acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 3 articles about acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 82.0%

perbenzyl fucosyl bromide (33639-77-9) + Acetic acid (2S,4aR,6S,7R,8S,8aS)-8-acetoxy-6-[(2R,3S,4R,5R,6R)-6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (219703-41-0) → acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (219703-42-1)

Guidance literature:

With tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)02104-2

Reference yield:

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (107823-72-3) → acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (219703-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / TMSTfO / CH₂Cl₂ / -25 °C

2: 82 percent / diisopropylethylamine, tetraethylammonium bromide / CH₂Cl₂ / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0040-4039(98)02104-2

Reference yield:

O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (129753-04-4) → acetic acid 8-acetoxy-6-[6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (219703-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / TMSTfO / CH₂Cl₂ / -25 °C

2: 82 percent / diisopropylethylamine, tetraethylammonium bromide / CH₂Cl₂ / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0040-4039(98)02104-2

upstream raw materials:

perbenzyl fucosyl bromide

Acetic acid (2S,4aR,6S,7R,8S,8aS)-8-acetoxy-6-[(2R,3S,4R,5R,6R)-6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Downstream raw materials:

C₆₇H₆₇Cl₃N₂O₁₈

acetic acid 8-acetoxy-6-[2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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