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

Base Information

• Chemical Name: allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside
• CAS No.: 1240486-90-1
• Molecular Formula: C₂₈H₄₆O₇Si
• Molecular Weight: 522.755
• Mol file: 1240486-90-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-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: 79.0%

allyl 3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside (1240486-89-8) + (S)-(+)-2-methylbutyric anhydride (84131-91-9) → allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside (1240486-90-1)

Guidance literature:

With pyridine; dmap; for 24h; Inert atmosphere;

DOI:10.1021/jo101231r

Reference yield: 79.0%

allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside (1240486-90-1) → allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-α-L-rhamnopyranoside (1240486-91-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 30 ℃; Inert atmosphere;

DOI:10.1021/jo101231r

Reference yield:

allyl 2-O-2(S)-methylbutyryl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside (1240486-90-1) → 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 (1448686-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ammonium cerium (IV) nitrate / water; acetonitrile / 3 h / 0 - 20 °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

5.1: palladium dichloride; sodium acetate / acetic acid; water / 30 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / 0 °C

With dmap; ammonium cerium (IV) nitrate; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; palladium dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/ol4020255

upstream raw materials:

allyl 3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranoside

(S)-(+)-2-methylbutyric anhydride

Downstream raw materials:

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

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

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