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

Base Information

Chemical Name: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
CAS No.:1026022-11-6
Molecular Formula:C₃₃H₅₂O₁₀Si
Molecular Weight:636.855
Hs Code.:

Synonyms: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

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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)]-2-O-t-butyldimethylsilyl-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)]-2-O-t-butyldimethylsilyl-α-D-fucopyranoside

There total 5 articles about 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 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: 84.0%

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

: 219808-89-6
4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranose

: 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

Guidance literature:: 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranose; With 2,4,6-tri-tertbutylpyridine; trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 - -45 ℃; for 2h;

O-allyl 4-O-acetyl-2-O-t-butyldimethylsilyl-α-D-fucopyranoside; In dichloromethane; at -45 - 23 ℃; for 16h; Further stages.;
DOI:10.1021/ja801008m

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 1026022-08-1
O-allyl 2-O-t-butyldimethylsilyl-3-O-p-methoxybenzyl-α-D-fucopyranoside

: 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

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 23 °C

3.1: 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 2 h / -78 - -45 °C

3.2: 16 h / -45 - 23 °C

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