methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 194347-75-6
• Molecular Formula: C₂₃H₂₆O₆S
• Molecular Weight: 430.522
• Mol file: 194347-75-6.mol

Synonyms:methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 12 articles about methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-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: 98.0%

Trimethyl(methylthio)silane (3908-55-2) + 1,2-di-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranose (406460-58-0) → methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside (194347-75-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1081/CAR-100108276

Reference yield: 70.0%

acetic anhydride (108-24-7) + benzyl bromide (100-39-0) + methyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside (194347-74-5) → methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside (194347-75-6)

Guidance literature:

methyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside; With di(n-butyl)tin oxide; In benzene; for 5h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In benzene; at 50 ℃; for 6h;

acetic anhydride; In pyridine; at 0 - 20 ℃; for 0.333333h; Further stages.;

DOI:10.1002/ejoc.200300149

Reference yield:

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (115678-10-9) → methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside (194347-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / pyridine / 17 h / 20 °C

2.1: 85 percent / trifluoroacetic acid / methanol / 4.5 °C / Heating

3.1: n-dibuthyltin oxide / benzene / 5 h / Heating

3.2: n-tetrabutylammonium iodide / benzene / 6 h / 50 °C

3.3: 70 percent / pyridine / 0.33 h / 0 - 20 °C

With di(n-butyl)tin oxide; trifluoroacetic acid; In pyridine; methanol; benzene;

DOI:10.1002/ejoc.200300149

upstream raw materials:

acetic anhydride

Trimethyl(methylthio)silane

1,2-di-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranose

benzyl bromide

Downstream raw materials:

Benzoic acid (2S,3aR,5S,6S,7R,7aR)-7-benzyloxy-2-methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

methyl (2-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate

2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol

isopropyl 4-O-benzoyl-3-O-benzyl-6-deoxy-β-L-arabino-hexopyranosid-2-ulose