(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

Base Information

Chemical Name:(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane
CAS No.:852610-43-6
Molecular Formula:C₂₁H₂₄O₃
Molecular Weight:324.42
Hs Code.:

Synonyms:(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

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Chemical Property of (1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

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Technology Process of (1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

There total 7 articles about (1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane 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: 85.0%

: 852610-42-5
(3S,4S)-bis(benzyloxymethyl)-1-cyclopentene

: 852610-43-6
(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 6h;
DOI:10.1021/jo0502504

Reference yield:

: 852610-39-0
methyl (1S,2S)-2-formylcyclopent-3-ene-1-carboxylate

: 852610-43-6
(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / lithium aluminum hydride / diethyl ether / 1 h / 0 - 20 °C

2: 75 percent / NaH; HMPA / tetrahydrofuran; various solvent(s) / 6 h / Heating

3: 85 percent / m-CPBA / 1,2-dichloro-ethane / 6 h / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane;
DOI:10.1021/jo0502504

Reference yield:

: 852610-52-7
(1S,2S)-2-((S)-1,2-Dihydroxy-ethyl)-cyclopent-3-enecarboxylic acid methyl ester

: 852610-43-6
(1S,2S,3S,5R)-2,3-bis[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 4 steps

1: 350 mg / NaIO₄ / methanol; H₂O / 1 h / 20 °C

2: 68 percent / lithium aluminum hydride / diethyl ether / 1 h / 0 - 20 °C

3: 75 percent / NaH; HMPA / tetrahydrofuran; various solvent(s) / 6 h / Heating

4: 85 percent / m-CPBA / 1,2-dichloro-ethane / 6 h / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; lithium aluminium tetrahydride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; water; 1,2-dichloro-ethane;
DOI:10.1021/jo0502504