(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

Base Information

Chemical Name:(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol
CAS No.:906641-18-7
Molecular Formula:C₂₆H₃₆O₄Si
Molecular Weight:440.655
Hs Code.:

Synonyms:(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

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Chemical Property of (1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

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Technology Process of (1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

There total 11 articles about (1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol 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: 95.0%

: 906641-17-6
[(1R,4S,5R,6S)-5,6-bis(benzyloxy)-4-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-yl]oxy(tert-butyl)dimethylsilane

: 906641-18-7
(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 3h;
DOI:10.3390/10080901

Reference yield:

: 906641-09-6
(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-ol

: 906641-18-7
(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / Et₃N; DMAP / 21 h / 20 °C

2: 99 percent / AgF; pyridine / 20 h / 20 °C

3: 86 percent / PdCl₂ / dioxane; H₂O / 3 h / 60 °C

4: 95 percent / MsCl; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

5: CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

6: 95 percent / TfOH / diethyl ether / 0.17 h / 20 °C

7: 82 percent / aq. NaOH / methanol / 12 h / 20 °C

8: 95 percent / lutidine / CH₂Cl₂ / 0.17 h / 20 °C

9: 95 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; trifluorormethanesulfonic acid; lutidine; silver fluoride; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; 3: Ferrier-II rearrangement;
DOI:10.3390/10080901

Reference yield:

: 906641-13-2
(1R,5S,6R)-5,6-bis(benzyloxy)-4-oxocyclohex-2-en-1-yl benzoate

: 906641-18-7
(1S,4R,5S,6R)-5,6-bis(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

2: 95 percent / TfOH / diethyl ether / 0.17 h / 20 °C

3: 82 percent / aq. NaOH / methanol / 12 h / 20 °C

4: 95 percent / lutidine / CH₂Cl₂ / 0.17 h / 20 °C

5: 95 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; trifluorormethanesulfonic acid; lutidine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water;
DOI:10.3390/10080901