(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

Base Information

Chemical Name:(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone
CAS No.:282101-77-3
Molecular Formula:C₂₅H₅₂O₅Si₃
Molecular Weight:516.941
Hs Code.:

Synonyms:(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

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Chemical Property of (4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

Chemical Property:

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Technology Process of (4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

There total 6 articles about (4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-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: 84.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 282101-76-2
(4R,5S,6R)-2-Benzenesulfonyl-4,5,6-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

: 282101-77-3
(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

Guidance literature:: With tri-n-butyltin lithium; In tetrahydrofuran; at -78 - 40 ℃; for 72h;
DOI:10.7164/antibiotics.53.430

Reference yield:

: (3R,4S,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-trityloxymethyl-dihydro-furan-2-one

: 282101-77-3
(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / H₂ / Pd-C / CHCl₃ / 12 h / 20 °C

2.1: DCC; Py*TFA; DMSO / diethyl ether / 0.5 h / 20 °C

2.2: 73 percent / D-camphorsulfonic acid (CSA) / methanol / 15 h / 50 °C

3.1: 94 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 48 h / 40 °C

5.1: 70 percent / SnCl₄ / CH₂Cl₂ / 3 h / -78 °C

6.1: 84 percent / n-Bu₃SnLi / tetrahydrofuran / 72 h / -78 - 40 °C

With 2,6-dimethylpyridine; n-butyllithium; tri-n-butyltin lithium; hydrogen; pyridinium trifluroacetate; tin(IV) chloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; 1.1: deprotection / 2.1: Oxidation / 2.2: Methylation / 3.1: Addition / 4.1: Ring cleavage / 5.1: Cyclization / 6.1: Michael reaction;
DOI:10.7164/antibiotics.53.430

Reference yield:

: 282101-73-9
(3R,4S,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-dihydro-furan-2-one

: 282101-77-3
(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 steps

1.1: DCC; Py*TFA; DMSO / diethyl ether / 0.5 h / 20 °C

1.2: 73 percent / D-camphorsulfonic acid (CSA) / methanol / 15 h / 50 °C

2.1: 94 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 48 h / 40 °C

4.1: 70 percent / SnCl₄ / CH₂Cl₂ / 3 h / -78 °C

5.1: 84 percent / n-Bu₃SnLi / tetrahydrofuran / 72 h / -78 - 40 °C

With 2,6-dimethylpyridine; n-butyllithium; tri-n-butyltin lithium; pyridinium trifluroacetate; tin(IV) chloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Oxidation / 1.2: Methylation / 2.1: Addition / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Michael reaction;
DOI:10.7164/antibiotics.53.430