Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate

Base Information

• Chemical Name: Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate
• CAS No.: 636559-71-2
• Molecular Formula: C28H30O5S
• Molecular Weight: 478.609
• Mol file: 636559-71-2.mol

Synonyms:Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate

Chemical Property of Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate

There total 11 articles about Phenyl 6-deoxy-3,4-bis-O-(phenylmethyl)-1-thio-alpha-L-mannopyranoside acetate 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: 99.0%

acetic anhydride (108-24-7) + Phenyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (172296-66-1) → phenyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (636559-71-2)

Guidance literature:

With magnesium triflate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00561

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (636559-71-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / acetone / 1 h / 20 °C

2.1: acetic acid / water / 3 h / 90 °C

3.1: di(n-butyl)tin oxide; benzene / 5 h / Reflux

3.2: 2 h / 20 °C

4.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; camphor-10-sulfonic acid; di(n-butyl)tin oxide; acetic acid; benzene; In water; acetone;

DOI:10.1016/j.carres.2014.11.005

Reference yield:

L-rhamnose (73-34-7) → phenyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (636559-71-2)

Guidance literature:

Multi-step reaction with 9 steps

1: triethylamine / dmap / dichloromethane / 16 h / 20 °C

2: tin(IV) chloride / dichloromethane / 5 h / 0 °C

3: potassium carbonate / tetrahydrofuran; methanol / 16 h / 20 °C

4: toluene-4-sulfonic acid

5: sodium hydride / DMF (N,N-dimethyl-formamide)

6: trifluoroacetic acid / methanol / 16 h / 50 °C

7: toluene / 4 h / Heating / reflux

8: tetrabutylammomium bromide / 5 h / 50 °C

9: pyridine

With pyridine; tetrabutylammomium bromide; tin(IV) chloride; sodium hydride; triethylamine; trifluoroacetic acid; dmap; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; DMF (N,N-dimethyl-formamide); dichloromethane; toluene;

upstream raw materials:

acetic anhydride

Phenyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

C₈₅H₉₀O₁₂Si₃