cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
• CAS No.: 101648-50-4
• Molecular Formula: C₃₅H₄₄O₁₇S
• Molecular Weight: 768.79
• Mol file: 101648-50-4.mol

Synonyms:cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Chemical Property of cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

There total 4 articles about cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside 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: 47.0%

Cinnamyl bromide (4392-24-9) + 1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose (69685-27-4) → cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (101648-50-4)

Guidance literature:

With thiourea; potassium bisulfite; potassium carbonate; In hydrogen bromide; acetic acid; acetone;

Reference yield:

2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl bromide (69649-71-4) → cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (101648-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone / 6 h / Heating

2: K₂CO₃, K₂S₂O₅ / acetone; H₂O / 2 h / Ambient temperature

With potassium disulphite; potassium carbonate; In water; acetone;

DOI:10.1021/jm00387a021

Reference yield:

1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose (69685-27-4) → cinnamyl 2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (101648-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 33percent HBr / acetic acid / 1.5 h / 0 - 5 °C

2: acetone / 6 h / Heating

3: K₂CO₃, K₂S₂O₅ / acetone; H₂O / 2 h / Ambient temperature

With potassium disulphite; hydrogen bromide; potassium carbonate; In water; acetic acid; acetone;

DOI:10.1021/jm00387a021

upstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-carbamimidoylsulfanyl-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester; hydrobromide

Cinnamyl bromide

2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl bromide

1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose

Downstream raw materials:

cinnamyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside