3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

Base Information

Chemical Name:3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol
CAS No.:219864-05-8
Molecular Formula:C₃₆H₃₆O₅
Molecular Weight:548.679
Hs Code.:

Synonyms:3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

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Chemical Property of 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

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Technology Process of 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

There total 9 articles about 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol 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: 62.0%

: 81353-38-0
(trimethylsilylethynyl)tributyltin

: 3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose

: 219864-05-8
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

Guidance literature:: (trimethylsilylethynyl)tributyltin; 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose;

With sodium hydroxide;
DOI:10.1021/jo100928g

Reference yield:

: 81353-38-0
(trimethylsilylethynyl)tributyltin

: 3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-69-5,94943-10-9,83462-68-4
2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose

: 219864-05-8
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1016/S0040-4039(00)00403-2

Reference yield:

: 4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5
2,3,4,6-tetra-O-benzyl-D-mannopyranose

: 219864-05-8
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Ac₂O / dimethylsulfoxide / 7 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 5.52 g / tetrahydrofuran; hexane / 3.5 h

3.1: Et₃SiH; BF₃*Et₂O / acetonitrile; CH₂Cl₂ / -40 °C

4.1: TBAF

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic anhydride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1039/b516282c