(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

Base Information

Chemical Name:(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol
CAS No.:1543006-73-0
Molecular Formula:C₁₅H₂₂O₃
Molecular Weight:250.338
Hs Code.:

Synonyms:(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

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Chemical Property of (2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

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Technology Process of (2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

There total 1 articles about (2R,3S)-2-allyl-5-(benzyloxy)pentane-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: 62.0%

: 2622-05-1
allylmagnesium bromide

: 111466-55-8
((2S,3S)-3-(2-(benzyloxy)ethyl)oxiran-2-yl)methanol

: 1543006-73-0
(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

Guidance literature:: allylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

{(2S,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-yl}methanol; In tetrahydrofuran; at -40 - 0 ℃; for 1.5h; Inert atmosphere;

With sodium periodate; In tetrahydrofuran; water; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.12.078

Reference yield: 94.0%

: 1543006-73-0
(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

: 77-76-9
2,2-dimethoxy-propane

: 1543006-77-4
(4S,5R)-5-allyl-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2013.12.078

Reference yield:

: 1543006-73-0
(2R,3S)-2-allyl-5-(benzyloxy)pentane-1,3-diol

: 1543006-58-1
C₃₄H₄₆N₂O₇

Guidance literature:: Multi-step reaction with 15 steps

1.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; toluene / 4 h / 20 °C / Inert atmosphere

3.1: sodium periodate / tetrahydrofuran; aq. phosphate buffer / 0.75 h / 0 °C / pH Ca_. 7 / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

5.1: triethylamine; dmap / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: sodium azide / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere

7.1: acetic acid; water / 3 h / 100 °C / Inert atmosphere

8.1: triethylamine; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere

9.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

10.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

10.2: 36 h / Inert atmosphere; Reflux

11.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

13.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

13.2: 1 h / -78 - 0 °C / Inert atmosphere

14.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere

15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / Inert atmosphere

15.2: 8 h / 20 °C / Inert atmosphere

With dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; sodium azide; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2013.12.078