(R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid

Base Information

• Chemical Name: (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid
• CAS No.: 202824-37-1
• Molecular Formula: C₅₃H₇₆O₁₃
• Molecular Weight: 921.179
• Mol file: 202824-37-1.mol

Synonyms:(R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid

Chemical Property of (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid

There total 10 articles about (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid 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: 87.0%

(R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid (202824-36-0) → (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid (202824-37-1)

Guidance literature:

With water; acetic acid; at 100 ℃; for 2h;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside (128962-63-0,116391-11-8) → (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid (202824-37-1)

Guidance literature:

Multi-step reaction with 6 steps

1: N-iodosuccinimide, triflic acid

2: N-iodosuccinimide, triflic acid

3: 96 percent / Zn/AcOH / 1.5 h / 20 °C

4: 73 percent / DCC, DMAP / CH₂Cl₂ / 18 h

5: 96 percent / Zn/AcOH / 1.5 h / 20 °C

6: 87 percent / acetic acid, water / 2 h / 100 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; zinc; In dichloromethane;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid (202824-37-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / camphersulfonic acid / methanol / 18 h / Heating

2: molecular sieves 4 Angstroem, N-iodosuccinimide, triflic acid / 1,2-dichloro-ethane / 0.08 h / 0 °C

3: N-iodosuccinimide, triflic acid / 1,2-dichloro-ethane / 0.17 h / 0 °C

4: 96 percent / Zn/AcOH / 1.5 h / 20 °C

5: 73 percent / DCC, DMAP / CH₂Cl₂ / 18 h

6: 96 percent / Zn/AcOH / 1.5 h / 20 °C

7: 87 percent / acetic acid, water / 2 h / 100 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; zinc; In methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

upstream raw materials:

(R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid

ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside

phenyl 1-thio-α-L-rhamnopyranose

ethyl 1-thio-α-L-rhamnopyranoside

Downstream raw materials:

rhamnolipid