(2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 669695-14-1
• Molecular Formula: C₂₈H₃₂O₅S
• Molecular Weight: 480.625
• Mol file: 669695-14-1.mol

Synonyms:(2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

There total 1 articles about (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 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:

trityl chloride (76-83-5) + isopropyl β-D-thiogalactopyranoside (367-93-1) → (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (669695-14-1)

Guidance literature:

With pyridine; dmap; at 80 ℃; for 16h;

DOI:10.1039/b108399f

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (669695-14-1) → (2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1039/b108399f

Reference yield:

(2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (669695-14-1) → isopropyl 2,4-di-O-acetyl-3-O-tert-butyldimethylsilyl-6-O-trityl-1-thio-β-D-galactopyranoside (314038-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / pyridine; dimethylformamide / 20 °C

2: pyridine / 50 °C

With pyridine; 1H-imidazole; In pyridine; N,N-dimethyl-formamide; 1: Silylation / 2: Acetylation;

DOI:10.1021/ol000243w

upstream raw materials:

trityl chloride

isopropyl β-D-thiogalactopyranoside

Downstream raw materials:

isopropyl 2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside

isopropyl 2,4-di-O-benzoyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside

isopropyl 2,4-di-O-benzoyl-3-O-tert-butyldimethylsilyl-6-O-triphenylmethyl-1-thio-β-D-galactopyranoside

isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside