2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside

Base Information

• Chemical Name: 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside
• CAS No.: 136174-79-3
• Molecular Formula: C₃₇H₄₄O₈S₂Si
• Molecular Weight: 708.969
• Mol file: 136174-79-3.mol

Synonyms:2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside

Chemical Property of 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside

There total 3 articles about 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside 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: 60.0%

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-α-D-galactopyranose (136174-77-1) + β-naphthol (135-19-3) → 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside (136174-79-3) + 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-α-D-galacto-pyranoside (136174-97-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at -78 ℃; Yields of byproduct given;

DOI:10.1021/jo00020a003

Reference yield:

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-galactopyranose + β-naphthol (135-19-3) → 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside (136174-79-3) + 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-α-D-galacto-pyranoside (136174-97-5)

Guidance literature:

With 4 A molecular sieve; triphenylphosphine; diethylazodicarboxylate; In toluene; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) -78 deg, 1 h, 2.) -78 deg, 23 deg overnight;

DOI:10.1021/ja00113a013

Reference yield:

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal (136314-67-5) → 2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2-deoxy-2-(thiopheny)-6-O-tosyl-β-D-galacto-pyranoside (136174-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2) Ag₂CO₃ / 1) CCl₄, -20 deg C 2) THF, H₂O

2: 60 percent / Ph₃P, diethyl azodicarboxylate / toluene / -78 °C

With triphenylphosphine; silver carbonate; diethylazodicarboxylate; In toluene;

DOI:10.1021/jo00020a003

upstream raw materials:

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-α-D-galactopyranose

β-naphthol

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal

Downstream raw materials:

2-naphthyl 4-O-acetyl-3-O((tert-butyldimetyl)silyl)-2,6-dideoxy-6-iodo-2-(thiophenyl)-β-D-galacto-pyranoside

Acetic acid (2S,3R,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-6-(naphthalen-2-yloxy)-5-phenylsulfanyl-tetrahydro-pyran-3-yl ester