ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside
CAS No.:134662-17-2
Molecular Formula:C₆₅H₇₄O₁₃S
Molecular Weight:1095.36
Hs Code.:

Synonyms:ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

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Technology Process of ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 14 articles about ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-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: 93.0%

: 100-39-0
benzyl bromide

: 134662-16-1
ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-2-O-α-L-rhamnopyranosyl-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

: 134662-17-2
ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1016/0008-6215(91)80096-6

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4
1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

: 134662-17-2
ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / hydrazine acetate / dimethylformamide / 1 h

2: 90 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / Ambient temperature

3: trimethylsilyl triflate / CH₂Cl₂ / 0.08 h / -30 °C

4: sodium methoxide (pH 10) / methanol / 16 h

5: 93 percent / sodium hydride / dimethylformamide / 2 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; hydrazinium monoacetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80096-6

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 134662-17-2
ethyl 4-O-<3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranosyl>-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / p-toluenesulfonic acid / dimethylformamide / 2 h

2: trimethylsilyl triflate / CH₂Cl₂ / 0.08 h / -30 °C

3: sodium methoxide (pH 10) / methanol / 16 h

4: 93 percent / sodium hydride / dimethylformamide / 2 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80096-6