ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 115152-51-7
• Molecular Formula: C₃₁H₃₃NO₇S
• Molecular Weight: 563.672

Synonyms:ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

There total 3 articles about ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-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: 72.0%

ethyl 4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-50-6) → ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-51-7)

Guidance literature:

With aluminium trichloride; trimethylamine-borane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)01753-7

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / NaH; TBAI / tetrahydrofuran / Heating

2: 72 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran

With aluminium trichloride; trimethylamine-borane; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)01753-7

Reference yield:

p-methoxybenzyl chloride (824-94-2) → ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / NaH; TBAI / tetrahydrofuran / Heating

2: 72 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran

With aluminium trichloride; trimethylamine-borane; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)01753-7

upstream raw materials:

ethyl 4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

p-methoxybenzyl chloride

Downstream raw materials:

ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

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

N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(3-azido-propoxy)-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

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