(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

Base Information

Chemical Name:(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane
CAS No.:490021-06-2
Molecular Formula:C₁₆H₂₁ClO₃
Molecular Weight:296.794
Hs Code.:

Synonyms:(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

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Chemical Property of (2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

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Technology Process of (2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

There total 8 articles about (2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane 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: 83.0%

: 490021-05-1
{(2R,3R)-3-[(R)-2-(4-Methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxiranyl}-methanol

: 490021-06-2
(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

Guidance literature:: With tetrachloromethane; sodium hydrogencarbonate; triphenylphosphine; for 6h; Heating;
DOI:10.1021/ol020193q

Reference yield:

: 122622-90-6
Ethyl (+/-)-3-hydroxy-4-methyl-4-pentenoate

: 490021-06-2
(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

Guidance literature:: Multi-step reaction with 8 steps

1: 49 percent / t-BuOOH; L-(+)-DIPT; Ti(i-PrO)4 / CH₂Cl₂ / 24 h / -20 °C

2: 93 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 25 h / 20 °C

3: 93 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.17 h / -60 - 0 °C

5: 99 percent / LiCl; DBU / acetonitrile / 1 h / 0 - 20 °C

6: 92 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

7: t-BuOOH; D-(-)-DIPT; Ti(i-PrO)4 / CH₂Cl₂ / 6 h / -20 °C

8: 83 percent / PPh₃; NaHCO₃; CCl₄ / 6 h / Heating

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; oxalyl dichloride; L-(+)-diisopropyl tartrate; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Sharpless asymmetric epoxidation / 4: Swern oxidation / 5: Wittig reaction / 7: Sharpless asymmetric epoxidation;
DOI:10.1021/ol020193q

Reference yield:

: 122674-65-1
Ethyl (3R)-3-hydroxy-4-methyl-4-pentenoate

: 490021-06-2
(2S,3R)-2-Chloromethyl-3-[(R)-2-(4-methoxy-benzyloxy)-3-methyl-but-3-enyl]-oxirane

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 25 h / 20 °C

2: 93 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.17 h / -60 - 0 °C

4: 99 percent / LiCl; DBU / acetonitrile / 1 h / 0 - 20 °C

5: 92 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

6: t-BuOOH; D-(-)-DIPT; Ti(i-PrO)4 / CH₂Cl₂ / 6 h / -20 °C

7: 83 percent / PPh₃; NaHCO₃; CCl₄ / 6 h / Heating

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 3: Swern oxidation / 4: Wittig reaction / 6: Sharpless asymmetric epoxidation;
DOI:10.1021/ol020193q