(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

Base Information

Chemical Name:(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester
CAS No.:349583-71-7
Molecular Formula:C₄₁H₇₀O₆Si₃
Molecular Weight:743.26
Hs Code.:

(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

Synonyms:(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

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Chemical Property of (2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

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Technology Process of (2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

There total 8 articles about (2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl 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: 66.0%

: 600-22-6
pyruvic acid methyl ester

: 349583-69-3
(3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene

: (E)-(2R,6R,9S)-9-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,9-dimethyl-6-triethylsilanyloxy-undec-4-enoic acid methyl ester

: 349583-71-7
(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/ol0160250

Reference yield:

: 1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-7-dimethyl-phenyl-silanyl-non-8-ene-6-ol

: 349583-71-7
(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 36.5 h / 23 °C

2: 66 percent / SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; tin(IV) chloride; triethylamine; In dichloromethane;
DOI:10.1021/ol0160250

Reference yield:

: 82188-73-6
(2S,3S)-2,3-epoxygeraniol

: 349583-71-7
(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Red-Al / tetrahydrofuran / 0 °C

2.1: PPTS / benzene / Heating

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: Et₃N; DMAP

5.1: OsO₄; NMO / acetone / pH 7

5.2: Pb(OAc)4 / ethyl acetate

6.1: t-BuOK; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 - -45 °C

6.2: tetrahydrofuran; various solvent(s) / 0.75 h / -78 °C

6.3: 77 percent / tetrahydrofuran; various solvent(s) / -78 - 23 °C

7.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 36.5 h / 23 °C

8.1: 66 percent / SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; pyridinium p-toluenesulfonate; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; acetone; benzene;
DOI:10.1021/ol0160250