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

Base Information

• Chemical Name: 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal
• CAS No.: 136314-67-5
• Molecular Formula: C₂₁H₃₂O₇SSi
• Molecular Weight: 456.632
• Mol file: 136314-67-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal 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: 37.0%

acetic anhydride (108-24-7) + Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-ylmethyl ester → 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal (136314-67-5)

Guidance literature:

With dmap; at 23 ℃; for 5h;

DOI:10.1021/ja00113a013

Reference yield:

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal (136314-67-5) + benzenesulfenyl chloride (931-59-9) → Acetic acid (2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-6-chloro-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:

In tetrachloromethane; at 23 ℃; for 1h;

DOI:10.1021/ja00113a013

Reference yield:

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-6-O-tosyl-D-galactal (136314-67-5) → 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 (136174-82-8)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: NaI / tetrahydrofuran

With triphenylphosphine; silver carbonate; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1021/jo00020a003

upstream raw materials:

acetic anhydride

Downstream raw materials:

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

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

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

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