(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

Base Information

Chemical Name:(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol
CAS No.:1266251-38-0
Molecular Formula:C₇H₁₂O₃
Molecular Weight:144.17
Hs Code.:

Synonyms:(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

Chemical Property:

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Technology Process of (1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

There total 10 articles about (1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-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:

: C₇H₁₀O₃

: 1266251-38-0
(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1007/s12039-010-0066-z

Reference yield:

: 1266251-28-8
(S)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-3-enyl acetate

: 1266251-38-0
(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: lithium hydrochloride monohydrate / methanol / 3 h / -5 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

5: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7: lithium hydrochloride monohydrate / methanol / 1 h / 0 °C / Inert atmosphere

8: acetic acid / water / 4 h / 70 °C / Inert atmosphere

9: sodium periodate / methanol; water / 0.5 h / Inert atmosphere; Cooling with ice

10: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; 6: Mitsunobu reaction;
DOI:10.1007/s12039-010-0066-z

Reference yield:

: 1266251-29-9
(4S,5S)-4-hydroxy-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enone

: 1266251-38-0
(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

2: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4: lithium hydrochloride monohydrate / methanol / 1 h / 0 °C / Inert atmosphere

5: acetic acid / water / 4 h / 70 °C / Inert atmosphere

6: sodium periodate / methanol; water / 0.5 h / Inert atmosphere; Cooling with ice

7: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; 3: Mitsunobu reaction;
DOI:10.1007/s12039-010-0066-z