2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester
CAS No.:125024-16-0
Molecular Formula:C₄₀H₆₆O₁₀Si
Molecular Weight:735.044
Hs Code.:

2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Synonyms:2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

There total 32 articles about 2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl 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: 85.0%

: 125024-14-8
(2S,3S)-3-<<2-(trimethylsilyl)ethoxy>methoxy>-2-methyl-4-oxopentyl pivalate

: 125024-15-9
(2S,4S,6R,8R,9S)-8-((S)-sec-Butyl)-4-(4-methoxy-benzyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

: 125024-16-0
2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1021/ja00160a051

Reference yield:

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

: 125024-16-0
2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Guidance literature:: Multi-step reaction with 14 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

With chromium chloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00112a006

Reference yield:

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

: 125024-16-0
2,2-Dimethyl-propionic acid (2S,3S)-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]-6-hydroxy-2-methyl-4-oxo-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Guidance literature:: Multi-step reaction with 13 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

With chromium chloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00112a006