5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

Base Information

Chemical Name:5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol
CAS No.:351032-48-9
Molecular Formula:C₃₈H₃₆O₅
Molecular Weight:572.701
Hs Code.:

Synonyms:5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

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Chemical Property of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

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Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

There total 3 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol 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: 83.0%

: 351032-46-7
5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-1-(trimethylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol

: 351032-48-9
5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;
DOI:10.1002/1522-2675(20010418)84:4<939::AID-HLCA939>3.0.CO;2-A

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 351032-48-9
5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: MeLi; LiBr / tetrahydrofuran; hexane / 4.5 h / 20 °C

1.2: 8.55 g / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: BF₃*Et₂O; Et₃SiH / CH₂Cl₂; acetonitrile / 2.5 h / 0 °C

3.1: 83 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 0 °C

With triethylsilane; boron trifluoride diethyl etherate; methyllithium; sodium methylate; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;
DOI:10.1002/1522-2675(20010418)84:4<939::AID-HLCA939>3.0.CO;2-A

Reference yield:

: 351032-44-5
(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(4-trimethylsilanyl-buta-1,3-diynyl)-tetrahydro-pyran-2-ol

: 351032-48-9
5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,2,3,4-tetradeoxy-D-glycero-D-gulo-deca-1,3-diynitol

Guidance literature:: Multi-step reaction with 2 steps

1: BF₃*Et₂O; Et₃SiH / CH₂Cl₂; acetonitrile / 2.5 h / 0 °C

2: 83 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 0 °C

With triethylsilane; boron trifluoride diethyl etherate; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1002/1522-2675(20010418)84:4<939::AID-HLCA939>3.0.CO;2-A