(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Base Information

Chemical Name:(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol
CAS No.:205681-06-7
Molecular Formula:C₂₀H₃₄O₄Si
Molecular Weight:366.573
Hs Code.:

Synonyms:(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

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Technology Process of (1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

There total 12 articles about (1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol 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: 93.0%

: 205681-04-5
(1S,2S,3R,5R)-3-benzyloxy-1,5-bis(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)cyclohexane

: 205681-06-7
(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/jo972285c

Reference yield:

: 36616-60-1
(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

: 205681-06-7
(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: L-selectride / tetrahydrofuran / -65 °C

2.1: imidazole

3.1: OsO₄, KIO₄

3.2: MCPBA

4.1: K₂CO₃ / methanol

5.1: imidazole

6.1: LiTMP, Et₂AlCl / benzene

7.1: NaH / dimethylformamide

8.1: 9-BBN / tetrahydrofuran

9.1: TBAF / tetrahydrofuran

With 1H-imidazole; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; potassium metaperiodate; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; diethylaluminium chloride; L-Selectride; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene; 1.1: Reduction / 2.1: Substitution / 3.1: Oxidation / 3.2: Oxidation / 4.1: Hydrolysis / 5.1: Substitution / 6.1: Rearrangement / 7.1: Alkylation / 8.1: Addition / 9.1: Substitution;
DOI:10.1080/15257779908041504

Reference yield:

: 35692-59-2
(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

: 205681-06-7
(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: imidazole

2.1: OsO₄, KIO₄

2.2: MCPBA

3.1: K₂CO₃ / methanol

4.1: imidazole

5.1: LiTMP, Et₂AlCl / benzene

6.1: NaH / dimethylformamide

7.1: 9-BBN / tetrahydrofuran

8.1: TBAF / tetrahydrofuran

With 1H-imidazole; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; potassium metaperiodate; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; diethylaluminium chloride; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene; 1.1: Substitution / 2.1: Oxidation / 2.2: Oxidation / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Rearrangement / 6.1: Alkylation / 7.1: Addition / 8.1: Substitution;
DOI:10.1080/15257779908041504