8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

Base Information

Chemical Name:8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid
CAS No.:499139-88-7
Molecular Formula:C₃₁H₃₄O₈
Molecular Weight:534.606
Hs Code.:

Synonyms:8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

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Chemical Property of 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

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Technology Process of 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

There total 4 articles about 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid 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: 73.0%

: 406488-01-5
8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

: 499139-88-7
8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

Guidance literature:: With jones' reagent; In acetone; at 0 ℃; for 2h;
DOI:10.1016/S0008-6215(02)00206-9

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9
(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

: 499139-88-7
8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: TMSOTf / acetonitrile / 24 h / 4 °C

1.2: 87 percent / 2 h / 0 °C

2.1: 70 percent / NaIO₄; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 3 h / 20 °C

3.1: 73 percent / Jones' reagent / acetone / 2 h / 0 °C

With sodium periodate; osmium(VIII) oxide; jones' reagent; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0008-6215(02)00206-9

Reference yield:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 499139-88-7
8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / NaH / dimethylformamide / 20 h / 20 °C

2.1: TMSOTf / acetonitrile / 24 h / 4 °C

2.2: 87 percent / 2 h / 0 °C

3.1: 70 percent / NaIO₄; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: 73 percent / Jones' reagent / acetone / 2 h / 0 °C

With sodium periodate; osmium(VIII) oxide; jones' reagent; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0008-6215(02)00206-9