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

Base Information

Chemical Name:(1S,2S,3R,5R)-3-benzyloxy-1,5-bis(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)cyclohexane
CAS No.:205681-04-5
Molecular Formula:C₂₆H₄₈O₄Si₂
Molecular Weight:480.836
Hs Code.:

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

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

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

There total 11 articles about (1S,2S,3R,5R)-3-benzyloxy-1,5-bis(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)cyclohexane 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:

: 205681-03-4
(1S,3R,5R)-3-benzyloxy-1,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexane

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

Guidance literature:: With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran;
DOI:10.1080/15257779908041504

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; potassium metaperiodate; 2,2,6,6-tetramethylpiperidinyl-lithium; 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;
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

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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; potassium metaperiodate; 2,2,6,6-tetramethylpiperidinyl-lithium; 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;
DOI:10.1080/15257779908041504