2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

Base Information

Chemical Name:2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate
CAS No.:488099-66-7
Molecular Formula:C₃₄H₅₇ClO₉Si
Molecular Weight:673.36
Hs Code.:

2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

Synonyms:2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

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Chemical Property of 2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

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Technology Process of 2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

There total 21 articles about 2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate 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: 62.0%

: 488099-58-7
(2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal

: 488099-69-0
2'-chloroethyl (2R,3S,4S)-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]-5-oxoheptanoate

: 488099-66-7
2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

Guidance literature:: 2'-chloroethyl (2R,3S,4S)-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]-5-oxoheptanoate; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

(2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal; In dichloromethane; Further stages.;
DOI:10.1021/ol0272343

Reference yield:

: 30414-53-0
methyl propanoyl acetate

: 488099-66-7
2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 99 percent / H₂; Amberlyst 15 / (R)-Binap-Ru(II)Cl₂ / methanol / 100 °C / 3102.97 Torr

2.1: LDA / tetrahydrofuran / -78 °C

2.2: HMPA

3.1: LAH / diethyl ether / 0 °C

4.1: TsOH / benzene / Heating

5.1: DIBAL-H / CH₂Cl₂ / -78 °C

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

7.1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

8.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 23 °C

9.1: OsO₄; NMO / tetrahydrofuran; acetone; H₂O

9.2: Pb(OAc)4 / ethyl acetate

10.1: sodium chlorite / CH₂Cl₂ / 0 °C / pH 7

11.1: 77 percent / Cl₃C₆H₂COCl; Et₃N; DMAP

12.1: DDQ / CH₂Cl₂ / 0 °C / pH 7

13.1: TPAP; NMO

14.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / -78 °C

14.2: 62 percent / CH₂Cl₂

With dmap; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; Amberlyst 15; tetrapropylammonium perruthennate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; RuCl₂[(R)-BINAP]; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; benzene; 2.2: Frater-Seebach alkylation / 6.1: Swern oxidation / 11.1: Yamaguchi esterification;
DOI:10.1021/ol0272343

Reference yield:

: 66767-61-1
methyl 2R,3R-nilate

: 488099-66-7
2'-chloroethyl (2R,3S,4S,6R,7R,8E,10S,11R)-11-[(3,4-dimethoxybenzyl)oxy]-7-hydroxy-3-methoxy-5-oxo-2-[(tert-butyldimethylsilyl)oxy]-4,6,8,10-tetramethyldodec-8-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiAlH₄ / diethyl ether

2.1: TsOH / benzene / Heating

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

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

5.1: CH₂Cl₂ / 23 °C

6.1: DIBAL-H / CH₂Cl₂; hexane / -78 °C

7.1: SO₃-pyridine; DMSO; Et₃N / CH₂Cl₂

8.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / -78 °C

8.2: 62 percent / CH₂Cl₂

With lithium aluminium tetrahydride; oxalyl dichloride; pyridine-SO₃ complex; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; dichloromethane; benzene; 4.1: Swern oxidation / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol0272343