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

Base Information

• Chemical Name: 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
• CAS No.: 495391-16-7
• Molecular Formula: C₃₂H₃₄N₄O₈
• Molecular Weight: 602.644
• Mol file: 495391-16-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 67.0%

3-azidopropan-1-ol (72320-38-8) + ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-51-7) → 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 (495391-16-7)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate;

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) → 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 (495391-16-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 67 percent / NIS; TMSOTf

With N-iodo-succinimide; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

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

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside (115152-50-6) → 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 (495391-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran

2: 67 percent / NIS; TMSOTf

With N-iodo-succinimide; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; In tetrahydrofuran;

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

upstream raw materials:

3-azidopropan-1-ol

ethyl 6-O-benzyl-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

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

Downstream raw materials:

N-[6-[5-acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-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

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

C₅₉H₆₅N₅O₁₄Si