2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 213459-83-7
• Molecular Formula: C₃₃H₄₉NO₆SSi₂
• Molecular Weight: 643.992
• Mol file: 213459-83-7.mol

Synonyms:2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property of 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-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-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 2 articles about 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-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: 66.0%

isopropyldimethylsilyl chloride (3634-56-8) + ethyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (169048-88-8) → 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (213459-83-7)

Guidance literature:

With dmap; In pyridine; for 48h;

DOI:10.1016/S0008-6215(98)00087-1

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (213459-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaCNBH₃, 4 Angstroem molecular sieves, 1M HCl / tetrahydrofuran; diethyl ether / 2.5 h

2: 66 percent / 4-dimethylaminopyridine / pyridine / 48 h

With hydrogenchloride; dmap; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; pyridine; diethyl ether;

DOI:10.1016/S0008-6215(98)00087-1

Reference yield: 84.0%

2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (213459-83-7) + 5-azidopentyl 4-O-acetyl-2,6-di-O-benzyl-α-D-galactopyranoside (213459-77-9) → C58H78N4O13Si2 (213459-90-6)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 0.5h;

DOI:10.1016/S0008-6215(98)00087-1

upstream raw materials:

isopropyldimethylsilyl chloride

ethyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

Downstream raw materials:

C₅₈H₇₈N₄O₁₃Si₂

Acetic acid (2R,3S,4S,5R,6S)-6-(5-azido-pentyloxy)-5-benzyloxy-2-benzyloxymethyl-4-[(2S,3R,4R,5S,6R)-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl ester