2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate

Base Information

• Chemical Name: 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate
• CAS No.: 488099-68-9
• Molecular Formula: C₂₆H₄₅ClO₇Si
• Molecular Weight: 533.178
• Mol file: 488099-68-9.mol

Synonyms:2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate

Chemical Property of 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate

There total 11 articles about 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate 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%

2-chloro-ethanol (107-07-3) + (2R,3S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxy)-3-methoxy-4-methyl-heptanoic acid → 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate (488099-68-9)

Guidance literature:

With dmap; triethylamine;

DOI:10.1021/ol0272343

Reference yield:

methyl propanoyl acetate (30414-53-0) → 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate (488099-68-9)

Guidance literature:

Multi-step reaction with 11 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

With dmap; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; Amberlyst 15; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 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:

2(R),3(R) methyl 3-hydroxy-2-methylpentanoate (78655-79-5) → 2'-chloroethyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate (488099-68-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LAH / diethyl ether / 0 °C

2.1: TsOH / benzene / Heating

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

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

5.1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

6.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 23 °C

7.1: OsO₄; NMO / tetrahydrofuran; acetone; H₂O

7.2: Pb(OAc)4 / ethyl acetate

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

9.1: 77 percent / Cl₃C₆H₂COCl; Et₃N; DMAP

With dmap; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; benzene; 4.1: Swern oxidation / 9.1: Yamaguchi esterification;

DOI:10.1021/ol0272343

upstream raw materials:

2-chloro-ethanol

methyl propanoyl acetate

2(R),3(R) methyl 3-hydroxy-2-methylpentanoate

methyl (3R)-3-hydroxypentanoate

Downstream raw materials:

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