allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:1092100-23-6
Molecular Formula:C₃₀H₄₀O₁₃
Molecular Weight:608.64
Hs Code.:

Synonyms:allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

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Technology Process of allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

There total 7 articles about allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-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: 95.0%

: 134136-22-4
allyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

: 122089-71-8
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 1092100-23-6
allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 6h;
DOI:10.1016/j.tet.2008.08.080

Reference yield:

: 73-34-7
L-rhamnose

: 1092100-23-6
allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: acetyl chloride / 0.25 h / 0 °C

1.2: 40 - 70 °C

2.1: toluene-4-sulfonic acid / acetone / 2 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -5 - 20 °C / Inert atmosphere

3.2: 4 h / -5 - 20 °C / Inert atmosphere

4.1: acetic acid / water / 3 h / 60 °C

5.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

5.2: 1 h / 20 °C / Cooling with ice

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6.5 h / -78 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; acetyl chloride; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;

Reference yield:

: 100-39-0
benzyl bromide

: 1092100-23-6
allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -5 - 20 °C / Inert atmosphere

1.2: 4 h / -5 - 20 °C / Inert atmosphere

2.1: acetic acid / water / 3 h / 60 °C

3.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

3.2: 1 h / 20 °C / Cooling with ice

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6.5 h / -78 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;