4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

Base Information

Chemical Name:4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose
CAS No.:887644-42-0
Molecular Formula:C₃₉H₄₄O₆Si
Molecular Weight:636.86
Hs Code.:

Synonyms:4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

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Chemical Property of 4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

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Technology Process of 4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

There total 2 articles about 4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose 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:

: 82598-88-7
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

: 1066-54-2
trimethylsilylacetylene

: 887644-42-0
4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

Guidance literature:: With n-butyllithium; cerium(III) chloride; Yield given; Multistep reaction; 1) THF, hexane, -78 deg C, 45 min; 2) THF, hexane, -78 deg C, 30 min; 3) THF, hexane, -78 deg C --> rt, 2 h;
DOI:10.1021/jo980517h

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

: 887644-42-0
4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; acetic anhydride; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1039/b516282c

Reference yield: 81.0%

: 887644-42-0
4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-mannooct-3-ulopyranose

: 219864-02-5
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-galactooctitol

Guidance literature:: With tris-(trimethylsilyl)silane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at 0 ℃; for 1.5h;
DOI:10.1039/b516282c