(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

Base Information

Chemical Name:(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran
CAS No.:349583-86-4
Molecular Formula:C₂₇H₃₈O₅
Molecular Weight:442.596
Hs Code.:

Synonyms:(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

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Chemical Property of (2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

Chemical Property:

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Technology Process of (2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

There total 12 articles about (2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-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: 99.0%

: 349583-75-1
(2R,4R,5R,6R',3S')-2-benzyloxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

: 349583-86-4
(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

Guidance literature:: With 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; In water; dimethyl sulfoxide; at 85 ℃; for 84h;
DOI:10.1021/ol0160250

Reference yield:

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

: 349583-86-4
(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 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

4: 82 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 19 h / Heating

5: 99 percent / KOt-Bu; 18-crown-6; TBAF*3H₂O / dimethylsulfoxide; H₂O / 84 h / 85 °C

With dmap; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/ol0160250

Reference yield:

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

: 349583-86-4
(2R,5R,6'R,3'S)-2-benzyloxymethyl-2-methyl-5-[1',6'-dihydroxy-3'-benzyloxy-3'-methyl-6'-hex-6'-yl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 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

10.1: 82 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 19 h / Heating

11.1: 99 percent / KOt-Bu; 18-crown-6; TBAF*3H₂O / dimethylsulfoxide; H₂O / 84 h / 85 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone; benzene;
DOI:10.1021/ol0160250