(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

Base Information

Chemical Name:(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran
CAS No.:349583-84-2
Molecular Formula:C₄₀H₇₀O₅Si₃
Molecular Weight:715.249
Hs Code.:

(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

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

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

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

There total 9 articles about (2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran 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:

: 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

: 349583-84-2
(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ol0160250

Reference yield:

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

: 349583-84-2
(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: DIBAL-H / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

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

Reference yield:

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

: 349583-84-2
(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 9 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

9.1: DIBAL-H / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °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