ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside

Base Information

• Chemical Name: ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside
• CAS No.: 152174-29-3
• Molecular Formula: C₄₂H₅₀O₈S
• Molecular Weight: 714.92
• Mol file: 152174-29-3.mol

Synonyms:ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside

Chemical Property of ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside

There total 13 articles about ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-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: 100.0%

ethyl 2-O-(3'-O-acetyl-2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside (152174-34-0) → ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside (152174-29-3)

Guidance literature:

With sodium methylate; In methanol; for 4h; Ambient temperature;

DOI:10.1139/v93-275

Reference yield:

methyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside (109526-95-6) → ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside (152174-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (di-n-butyl)tin oxide, 2.) tetra-n-butylammonium iodide / 1.) benzene, toluene, reflux, 5 h, 2.) toluene, reflux, 3 h

2: 1.) 3percent H₂SO₄, 2.) pyridine / 1.) AcOH, H₂O, acetone, reflux, 20 h, 2.) RT, 4 h

3: 100 percent / HCl (gas) / CH₂Cl₂; acetic acid / 4 h / 0 °C

4: 92 percent / acetone / 0.17 h / Ambient temperature

5: 1.) 4 A molecular sieves, silver triflate / 1.) CH₂Cl₂, -10 deg C, 2.) CH₂Cl₂, a) -5 to -10 deg C, 30 min, b) RT, 5 h

6: 100 percent / 0.5percent CH₃ONa / methanol / 4 h / Ambient temperature

With pyridine; hydrogenchloride; 4 A molecular sieve; sulfuric acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In methanol; dichloromethane; acetic acid; acetone;

DOI:10.1139/v93-275

Reference yield:

benzyl bromide (100-39-0) → ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside (152174-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (di-n-butyl)tin oxide, 2.) tetra-n-butylammonium iodide / 1.) benzene, toluene, reflux, 5 h, 2.) toluene, reflux, 3 h

2: 1.) 3percent H₂SO₄, 2.) pyridine / 1.) AcOH, H₂O, acetone, reflux, 20 h, 2.) RT, 4 h

3: 100 percent / HCl (gas) / CH₂Cl₂; acetic acid / 4 h / 0 °C

4: 92 percent / acetone / 0.17 h / Ambient temperature

5: 1.) 4 A molecular sieves, silver triflate / 1.) CH₂Cl₂, -10 deg C, 2.) CH₂Cl₂, a) -5 to -10 deg C, 30 min, b) RT, 5 h

6: 100 percent / 0.5percent CH₃ONa / methanol / 4 h / Ambient temperature

With pyridine; hydrogenchloride; 4 A molecular sieve; sulfuric acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In methanol; dichloromethane; acetic acid; acetone;

DOI:10.1139/v93-275

upstream raw materials:

ethyl 2-O-(3'-O-acetyl-2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

methyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside

methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside

benzyl bromide

Downstream raw materials:

ethyl 2-O-<3'-O-(3''-O-acetyl-2'',4''-di-O-benzyl-α-D-rhamnopyranosyl)-2',4'-di-O-benzyl-α-D-rhamnopyranosyl>-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

11-(methoxycarbonyl)undecyl 2-O-<3'-O-(3''-O-acetyl-2'',4''-di-O-benzyl-α-D-rhamnopyranosyl)-2',4'-di-O-benzyl-α-D-rhamnopyranosyl>-3,4-di-O-benzyl-α-D-rhamnopyranoside