allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside
• CAS No.: 1448686-68-7
• Molecular Formula: C₇₀H₁₀₆O₁₇
• Molecular Weight: 1219.6
• Mol file: 1448686-68-7.mol

Synonyms:allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside

Chemical Property of allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside

There total 8 articles about allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-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: 90.0%

2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl trichloroacetimidate (1240486-88-7) + allyl 2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside (1448686-67-6) → allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside (1448686-68-7)

Guidance literature:

2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl trichloroacetimidate; allyl 2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside; In dichloromethane; at 20 ℃; for 0.166667h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 1.5h; Molecular sieve;

DOI:10.1021/ol4020255

Reference yield:

(S)-1-benzyloxy-11-hexadecanol (929296-51-5) → allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside (1448686-68-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 8 h / 0 °C

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 20 °C

3.1: Jones reagent / acetone / 3 h / 0 °C

4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 0 °C

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 35 °C

6.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

6.2: 1.5 h / -78 - 0 °C / Molecular sieve

With dmap; Jones reagent; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; acetone;

DOI:10.1021/ol4020255

Reference yield:

11(S)-levulinoyloxy-1-hexadecanol (1448686-64-3) → allyl 2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside (1448686-68-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Jones reagent / acetone / 3 h / 0 °C

2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 0 °C

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 35 °C

4.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

4.2: 1.5 h / -78 - 0 °C / Molecular sieve

With dmap; Jones reagent; tetrabutyl ammonium fluoride; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ol4020255

upstream raw materials:

allyl 2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside

2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl trichloroacetimidate

allyl 2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranoside

allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside

Downstream raw materials:

2-O-trans-cinnamoyl-3-O-p-methoxybenzyl-4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)-2-O-2(S)-methylbutyryl-3-O-(11(S)-levulinoyloxyhexadecanoyl)-α-L-rhamnopyranosyl trichloroacetimidate