(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

Base Information

• Chemical Name: (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
• CAS No.: 202824-36-0
• Molecular Formula: C₅₉H₈₆O₁₅
• Molecular Weight: 1035.32
• Mol file: 202824-36-0.mol

Synonyms:(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

Chemical Property of (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

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)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid

There total 9 articles about (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 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: 96.0%

C67H92O16 (202824-35-9) → (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)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 1.5h;

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)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid (202824-36-0)

Guidance literature:

Multi-step reaction with 5 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

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 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)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid (202824-36-0)

Guidance literature:

Multi-step reaction with 6 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

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; 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:

C₆₇H₉₂O₁₆

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:

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

rhamnolipid