(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

Base Information

Chemical Name:(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone
CAS No.:459423-88-2
Molecular Formula:C₂₀H₃₈O₅Si₂
Molecular Weight:414.69
Hs Code.:

Synonyms:(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

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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 (4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

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Technology Process of (4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

There total 5 articles about (4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone 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: 100.0%

: 108-24-7
acetic anhydride

: 396100-83-7
(4S,5R,6R)-4,5-bis(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-2-enone

: 459423-88-2
(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

Guidance literature:: With pyridine; at 20 ℃; for 16h;
DOI:10.1016/S0040-4020(02)00370-8

Reference yield:

: 255912-66-4
(1R,4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-en-1-ol

: 459423-88-2
(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

1: pyridinium chlorochromate

2: NaHMDS / tetrahydrofuran / 0.33 h / -78 °C

3: 100 percent / pyridine / 16 h / 20 °C

With pyridine; sodium hexamethyldisilazane; pyridinium chlorochromate; In tetrahydrofuran;
DOI:10.1016/S0040-4020(02)00370-8

Reference yield:

: 184377-26-2
(1SR,2RS,4RS,5SR)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexene oxide

: 459423-88-2
(4S,5R,6R)-6-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: n-butyllithium; N-methyl-N-[(1S,2R)-1-phenyl-2-pyrrolidin-1-ylpropyl]amine / tetrahydrofuran; hexane / 20 h / 0 - 20 °C

2: pyridinium chlorochromate

3: NaHMDS / tetrahydrofuran / 0.33 h / -78 °C

4: 100 percent / pyridine / 16 h / 20 °C

With pyridine; n-butyllithium; sodium hexamethyldisilazane; pyridinium chlorochromate; (1S,2R)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine; In tetrahydrofuran; hexane;
DOI:10.1016/S0040-4020(02)00370-8