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

Base Information

• Chemical Name: 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
• CAS No.: 152174-31-7
• Molecular Formula: C₇₅H₉₄O₁₆
• Molecular Weight: 1251.56
• Mol file: 152174-31-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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:

benzyl bromide (100-39-0) → 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 (152174-31-7)

Guidance literature:

Multi-step reaction with 7 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

7: 66 mg / 4 A molecular sieves, N-iodosuccinimide, trifluoromethanesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 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) → 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 (152174-31-7)

Guidance literature:

Multi-step reaction with 6 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

6: 66 mg / 4 A molecular sieves, N-iodosuccinimide, trifluoromethanesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; 4 A molecular sives; sulfuric acid; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; acetic acid;

DOI:10.1139/v93-275

Reference yield:

3-O-acetyl-2,4-di-O-benzyl-α-D-rhamnopyranosyl chloride (112612-48-3) → 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 (152174-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 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

2: 100 percent / 0.5percent CH₃ONa / methanol / 4 h / Ambient temperature

3: 80 percent / 4 A molecular sives, silver triflate / CH₂Cl₂ / a) -10 to -5 deg C, 1 h, b) RT, overnight

4: 66 mg / 4 A molecular sieves, N-iodosuccinimide, trifluoromethanesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; 4 A molecular sives; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1139/v93-275

upstream raw materials:

benzyl bromide

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

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