5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

Base Information

Chemical Name:5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol
CAS No.:1426261-16-6
Molecular Formula:C₂₀H₃₀O₆
Molecular Weight:366.455
Hs Code.:

Synonyms:5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

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Chemical Property of 5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

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Technology Process of 5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

There total 3 articles about 5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol 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: 70.0%

: 141410-34-6
5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol

: 1426261-16-6
5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

Guidance literature:: 5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 6h; regioselective reaction;
DOI:10.1055/s-0032-1317932

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 1426261-16-6
5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 6 h / -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C

2.2: 6 h / 20 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

3.2: 6 h / 0 °C

With potassium tert-butylate; sodium hydride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1.1: |Wittig Olefination;
DOI:10.1055/s-0032-1317932

Reference yield:

: 137945-76-7
(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl][(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

: 1426261-16-6
5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C

1.2: 6 h / 20 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

2.2: 6 h / 0 °C

With sodium hydride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran;
DOI:10.1055/s-0032-1317932