2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester
CAS No.:125048-93-3
Molecular Formula:C₄₇H₇₂O₁₀SSi
Molecular Weight:857.234
Hs Code.:

2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

Synonyms:2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

There total 38 articles about 2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester 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: 90.0%

: 125024-19-3
2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfinyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

: 125048-93-3
2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

Guidance literature:: With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; In methanol; water; at 25 ℃; for 48h;
DOI:10.1021/ja00160a051

Reference yield:

: 1565-80-6
(2S)-2-methyl-1-butanol

: 125048-93-3
2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 15 min, 2.) CH₂Cl₂, RT

2: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

3: 86 percent / CH₂Cl₂ / 3 h

4: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

5: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

6: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

7: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

9: 88 percent / camphorsulfonic acid / 3 h / Ambient temperature

10: 86 percent / (n-Bu)4NF / tetrahydrofuran / 1 h / 50 °C

11: H₂ / Pd/BaSO₄ / methanol; quinoline / 0.5 h

12: camphorsulfonic acid / quinoline; diethyl ether / 0.25 h / Ambient temperature

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

14: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

15: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h

16: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

17: 93 percent / tetrahydrofuran / 0.5 h / 0 °C

18: 87 percent / Et₃N / CH₂Cl₂ / -78 °C

19: 88 percent / oxone / methanol; H₂O / 24 h / Ambient temperature

With dmap; chromium chloride; Oxone; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/ja00112a006

Reference yield:

: 1730-97-8
(S)-2-methylbutyraldehyde

: 125048-93-3
2,2-Dimethyl-propionic acid (E)-(2S,3S)-6-benzenesulfonyl-6-[(2S,4S,6R,8R,9S)-8-((S)-sec-butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-2,4-dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-hex-4-enyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 86 percent / CH₂Cl₂ / 3 h

3: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

4: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

5: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

6: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

8: 88 percent / camphorsulfonic acid / 3 h / Ambient temperature

9: 86 percent / (n-Bu)4NF / tetrahydrofuran / 1 h / 50 °C

10: H₂ / Pd/BaSO₄ / methanol; quinoline / 0.5 h

11: camphorsulfonic acid / quinoline; diethyl ether / 0.25 h / Ambient temperature

12: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

13: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

14: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h

15: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

16: 93 percent / tetrahydrofuran / 0.5 h / 0 °C

17: 87 percent / Et₃N / CH₂Cl₂ / -78 °C

18: 88 percent / oxone / methanol; H₂O / 24 h / Ambient temperature

With dmap; chromium chloride; Oxone; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/ja00112a006