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

Base Information

• Chemical Name: ethyl 2-O-(3'-O-acetyl-2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside
• CAS No.: 152174-34-0
• Molecular Formula: C₄₄H₅₂O₉S
• Molecular Weight: 756.957
• Mol file: 152174-34-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about ethyl 2-O-(3'-O-acetyl-2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-3,4-di-O-benzyl-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:

methyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside (109526-95-6) → 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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1139/v93-275

Reference yield:

benzyl bromide (100-39-0) → 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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1139/v93-275

Reference yield:

benzyl chloride (100-44-7) → 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)

Guidance literature:

Multi-step reaction with 7 steps

1: KOH / dimethylsulfoxide / 4 h / Ambient temperature

2: 60percent aq. CH₃COOH / 1 h / 100 °C

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

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

5: 100 percent / HCl (gas) / CH₂Cl₂; acetic acid / 4 h / 0 °C

6: 92 percent / acetone / 0.17 h / Ambient temperature

7: 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

With pyridine; hydrogenchloride; potassium hydroxide; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; acetic acid; In dichloromethane; acetic acid; dimethyl sulfoxide; acetone;

DOI:10.1139/v93-275

upstream raw materials:

ethyl 3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

3-O-acetyl-2,4-di-O-benzyl-α-D-rhamnopyranosyl chloride

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

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

Downstream raw materials:

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

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

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