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

Base Information

• Chemical Name: 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
• CAS No.: 152174-30-6
• Molecular Formula: C₆₄H₇₄O₁₃S
• Molecular Weight: 1083.35
• Mol file: 152174-30-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 80.0%

3-O-acetyl-2,4-di-O-benzyl-α-D-rhamnopyranosyl chloride (112612-48-3) + ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside (152174-29-3) → 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 (152174-30-6)

Guidance literature:

With 4 A molecular sives; silver trifluoromethanesulfonate; In dichloromethane; a) -10 to -5 deg C, 1 h, b) RT, overnight;

DOI:10.1139/v93-275

Reference yield:

benzyl bromide (100-39-0) → 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 (152174-30-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / tetra-n-butylammonium iodide, KOH / toluene / 4 h / Ambient temperature

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

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

4: 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

5: 100 percent / 0.5percent CH₃ONa / methanol / 4 h / Ambient temperature

6: 80 percent / 4 A molecular sives, silver triflate / CH₂Cl₂ / a) -10 to -5 deg C, 1 h, b) RT, overnight

With pyridine; hydrogenchloride; potassium hydroxide; 4 A molecular sieve; 4 A molecular sives; sulfuric acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; In methanol; dichloromethane; acetic acid; toluene;

DOI:10.1139/v93-275

Reference yield:

methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside (112612-46-1) → 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 (152174-30-6)

Guidance literature:

Multi-step reaction with 5 steps

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

2: HCl (gas) / CH₂Cl₂; acetic acid / 4 h / 0 °C

3: 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

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

5: 80 percent / 4 A molecular sives, silver triflate / CH₂Cl₂ / a) -10 to -5 deg C, 1 h, b) RT, overnight

With pyridine; hydrogenchloride; 4 A molecular sieve; 4 A molecular sives; sulfuric acid; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; acetic acid;

DOI:10.1139/v93-275

upstream raw materials:

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

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

benzyl bromide

methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside