(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

Base Information

Chemical Name:(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol
CAS No.:1450975-42-4
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

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Chemical Property of (-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

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Technology Process of (-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

There total 9 articles about (-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-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: 82.0%

: 1450975-41-3
(-)-(((3aR,4S,6R,6aR)-4-(benzyloxy)-2,2-dimethyltetrahydrospiro[cyclopenta[d][1,3] dioxole-5,1'-cyclopropan]-6-yl)methoxy)(tert-butyl)dimethylsilane

: 1450975-42-4
(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

Guidance literature:: With water; trifluoroacetic acid; at 50 ℃; for 3h;

Reference yield:

: 1450975-30-0
⁽¹⁾-tert-butyl(((3aR,4R,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methoxy)dimethylsilane

: 1450975-42-4
(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C

2.1: trimethylsulphonium iodide; n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -10 - 20 °C

3.1: Dess-Martin periodane / 1 h / 0 - 20 °C

4.1: CeCl₃*7H₂O / methanol / 0.17 h / -78 °C

4.2: 0.25 h / -78 °C

4.3: 1 h / 0 °C

5.1: diethylzinc / diethyl ether; hexane / 8 h / 0 - 20 °C

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

6.2: 3 h / 0 - 20 °C

7.1: water; trifluoroacetic acid / 3 h / 50 °C

With n-butyllithium; CeCl₃*7H₂O; trimethylsulphonium iodide; water; diethylzinc; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 1450975-31-1
(1)-tert-butyl(((1aR,1bR,4aR,5S,5aR)-3,3-dimethyltetrahydro-1aH-oxireno[2’,3’:3,4]-cyclopenta[1,2-d][1,3]dioxol-5-yl)methoxy)dimethylsilane

: 1450975-42-4
(-)-(4S,5R,6R,7R)-4-(benzyloxy)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: trimethylsulphonium iodide; n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -10 - 20 °C

2.1: Dess-Martin periodane / 1 h / 0 - 20 °C

3.1: CeCl₃*7H₂O / methanol / 0.17 h / -78 °C

3.2: 0.25 h / -78 °C

3.3: 1 h / 0 °C

4.1: diethylzinc / diethyl ether; hexane / 8 h / 0 - 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C

6.1: water; trifluoroacetic acid / 3 h / 50 °C

With n-butyllithium; CeCl₃*7H₂O; trimethylsulphonium iodide; water; diethylzinc; sodium hydride; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; mineral oil;