(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

Base Information

Chemical Name:(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one
CAS No.:328074-57-3
Molecular Formula:C₂₇H₄₀O₆
Molecular Weight:460.611
Hs Code.:

Synonyms:(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

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Chemical Property of (E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

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Technology Process of (E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

There total 16 articles about (E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one 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: 77.0%

: 328074-56-2
3-Hydroxy-1-{(2R,3R)-3-[4-(4-methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hexan-1-one

: 328074-57-3
(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

Guidance literature:: With dmap; methanesulfonyl chloride; In dichloromethane;
DOI:10.1039/b007617l

Reference yield:

: (Z)-(R)-7-(tert-Butyl-dimethyl-silanyloxy)-oct-5-en-1-ol

: 328074-57-3
(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / DMAP; pyridine

2.1: 98 percent / Bu₄NF / tetrahydrofuran

3.1: 100 percent / MCPBA / CH₂Cl₂ / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: Na[PhSeB(OET)3] / acetic acid; ethanol / 0 °C

6.1: (CH₃CH₂)2BOCH₃; NaBH₄ / tetrahydrofuran; methanol

7.1: PPTS / CH₂Cl₂

8.1: 98 percent / NH₃ / methanol

9.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

10.1: LiHMDS / tetrahydrofuran / -78 °C

10.2: 63 percent / tetrahydrofuran

11.1: 77 percent / CH₃SO₂Cl; DMAP / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; diethyl methoxy borane; tetrabutyl ammonium fluoride; ammonia; pyridinium p-toluenesulfonate; dimethyl sulfoxide; methanesulfonyl chloride; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; 4.1: Swern oxidation / 9.1: Swern oxidation;
DOI:10.1039/b007617l

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 328074-57-3
(E)-1-{(2R,3R)-3-[4-(4-Methoxy-benzyloxy)-butyl]-oxiranyl}-6-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-hex-2-en-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: PPTS / CH₂Cl₂

2.1: Bu₄NF / tetrahydrofuran

3.1: 88 percent / MCPBA / CH₂Cl₂ / 0 °C

4.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: LiHMDS / tetrahydrofuran / -78 °C

5.2: 63 percent / tetrahydrofuran

6.1: 77 percent / CH₃SO₂Cl; DMAP / CH₂Cl₂

With dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1039/b007617l