Ethyl 2,3-O-isopropylidene-1-thio-a-L-rhamnopyranoside

Base Information

• Chemical Name: Ethyl 2,3-O-isopropylidene-1-thio-a-L-rhamnopyranoside
• CAS No.: 145124-97-6
• Molecular Formula: C₁₁H₂₀O₄S
• Molecular Weight: 248.343
• Mol file: 145124-97-6.mol

Synonyms:4H-1,3-Dioxolo[4,5-c]pyran,a-D-mannopyranoside deriv.

Chemical Property of Ethyl 2,3-O-isopropylidene-1-thio-a-L-rhamnopyranoside

Chemical Property:

• Boiling Point: 375.6±42.0 °C(Predicted)
• PKA: 13.20±0.70(Predicted)
• PSA: 73.22000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 1.36530

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 2,3-O-isopropylidene-1-thio-a-L-rhamnopyranoside

There total 5 articles about Ethyl 2,3-O-isopropylidene-1-thio-a-L-rhamnopyranoside 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: 81.0%

Ethyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (145124-96-5) → ethyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside (145124-97-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; benzene; for 0.166667h; Heating;

DOI:10.1016/0008-6215(93)80060-R

Reference yield: 55.4%

ethyl 6-deoxy-6-iodo-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside (887478-20-8) → ethyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside (145124-97-6)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; at 20 ℃; for 96h;

DOI:10.1080/07328300500495878

Reference yield:

ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside (151669-30-6) → ethyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside (145124-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.3 percent / iodine; triphenylphosphine; imidazole / toluene / Heating

2: 55.4 percent / hydrogen; triethylamine / palladium on carbon / ethanol / 96 h / 20 °C

With 1H-imidazole; hydrogen; iodine; triethylamine; triphenylphosphine; palladium on activated charcoal; In ethanol; toluene;

DOI:10.1080/07328300500495878

upstream raw materials:

Ethyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

ethyl 6-deoxy-6-iodo-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside

ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

ethyl 1-thio-α-D-mannopyranoside

Downstream raw materials:

Ethyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside

Ethyl 3-O-acetyl-4-O-benzyl-2-O-methyl-1-thio-α-D-rhamnopyranoside

Ethyl 4-O-benzyl-2-O-methyl-1-thio-α-D-rhamnopyranoside

ethyl 3-O-benzyl-2-O-chloroacetyl-4-O-methyl-1-thio-α-D-rhamnopyranoside

Refernces

• 1、 Kerekgyarto, Janos,Szurmai, Zoltan,Liptak, Andras. "Synthesis of p-trifluoroacetamidophenyl 6-deoxy-2-O--α-L-rhamnopyranosyl>-α-L-talopyranoside: a spacer armed tetrasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 2". . p. 65 - 80. Retrieved 2007/10/02.