O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

Base Information

Chemical Name:O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside
CAS No.:1026022-12-7
Molecular Formula:C₂₇H₃₈O₁₀
Molecular Weight:522.593
Hs Code.:

Synonyms:O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

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Chemical Property of O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

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Technology Process of O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

There total 7 articles about O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside 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%

: 1026022-11-6
O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-2-O-t-butyldimethylsilyl-α-D-fucopyranoside

: 1026022-12-7
O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 4h;
DOI:10.1021/ja801008m

Reference yield:

: 1026022-07-0
allyl 3-O-p-methoxybenzyl-α-D-fucopyranoside

: 1026022-12-7
O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole; dmap / dichloromethane / 27 h / 23 °C

2.1: dmap; triethylamine / dichloromethane / 22.5 h / 23 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 23 °C

4.1: 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 2 h / -78 - -45 °C

4.2: 16 h / -45 - 23 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 23 °C

With 1H-imidazole; dmap; 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;

Reference yield:

: 1026022-10-5
O-allyl 4-O-acetyl-2-O-t-butyldimethylsilyl-α-D-fucopyranoside

: 1026022-12-7
O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 2 h / -78 - -45 °C

1.2: 16 h / -45 - 23 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 23 °C

With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;