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

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Chemical Name:ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside
CAS No.:134662-15-0
Molecular Formula:C₃₈H₄₆O₉S
Molecular Weight:678.844
Hs Code.:

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

There total 7 articles about ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-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: 79.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 134662-14-9
ethyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

: 134662-15-0
ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 2h;
DOI:10.1016/0008-6215(91)80096-6

Reference yield:

: 93274-52-3
methyl 3-O-allyl-β-D-galactopyranoside

: 134662-15-0
ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / pyridine / 16 h / Ambient temperature

2: conc. sulfuric aicd / 1.5 h / 0 °C

3: 28 percent / hydrazine acetate / dimethylformamide / 2 h / Ambient temperature

4: 78 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

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

6: sodium methoxide / methanol / 16 h

7: 79 percent / p-toluenesulfonic acid / dimethylformamide / 2 h

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80096-6

Reference yield:

: 134662-12-7,134662-31-0
2,4,6-tri-O-acetyl-3-O-allyl-α,β-D-galactopyranose

: 134662-15-0
ethyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

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

3: sodium methoxide / methanol / 16 h

4: 79 percent / p-toluenesulfonic acid / dimethylformamide / 2 h

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80096-6