(3S,5S)-5-(benzyloxy)octane-1,3-diol

Base Information

Chemical Name:(3S,5S)-5-(benzyloxy)octane-1,3-diol
CAS No.:1446447-10-4
Molecular Formula:C₁₅H₂₄O₃
Molecular Weight:252.354
Hs Code.:

Synonyms:(3S,5S)-5-(benzyloxy)octane-1,3-diol

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Chemical Property of (3S,5S)-5-(benzyloxy)octane-1,3-diol

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Technology Process of (3S,5S)-5-(benzyloxy)octane-1,3-diol

There total 6 articles about (3S,5S)-5-(benzyloxy)octane-1,3-diol 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: 80.0%

: 1446447-09-1
((2R,3R)-3-((S)-2-(benzyloxy)pentyl)oxiran-2-yl)methanol

: 1446447-10-4
(3S,5S)-5-(benzyloxy)octane-1,3-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at 0 ℃; for 5h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

: 1388220-70-9
(S)-((hept-1-en-4-yloxy)methyl)benzene

: 1446447-10-4
(3S,5S)-5-(benzyloxy)octane-1,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1: water; osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / 1,4-dioxane; toluene / 4.5 h / 0 - 20 °C / Inert atmosphere

2: dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 °C / Inert atmosphere

4: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate; p-cumenyl hydroperoxide / dichloromethane / 12 h / -20 °C / Inert atmosphere; Molecular sieve

5: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; p-cumenyl hydroperoxide; water; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; 2: |Wittig Olefination / 4: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

: 85520-72-5
(4S)-hept-1-en-4-ol

: 1446447-10-4
(3S,5S)-5-(benzyloxy)octane-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0 °C / Inert atmosphere

1.2: 4 h / 0 - 20 °C / Inert atmosphere

2.1: water; osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / 1,4-dioxane; toluene / 4.5 h / 0 - 20 °C / Inert atmosphere

3.1: dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 °C / Inert atmosphere

5.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate; p-cumenyl hydroperoxide / dichloromethane / 12 h / -20 °C / Inert atmosphere; Molecular sieve

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; p-cumenyl hydroperoxide; water; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; mineral oil; 3.1: |Wittig Olefination / 5.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetasy.2013.05.004