(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

Base Information

Chemical Name:(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol
CAS No.:1355670-48-2
Molecular Formula:C₃₄H₅₂O₄Si₂
Molecular Weight:580.955
Hs Code.:

Synonyms:(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

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Chemical Property of (1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

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Technology Process of (1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

There total 6 articles about (1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-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: 66.0%

: 1355670-46-0
(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one

: 1774-47-6
trimethylsulfoxonium iodide

: 1355670-48-2
(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

Guidance literature:: trimethylsulfoxonium iodide; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one; In tetrahydrofuran; at 0 - 20 ℃; for 5h; stereoselective reaction;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 915694-39-2
(+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol

: 1355670-48-2
(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 1 h / -78 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.2: 5 h / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 915694-38-1
(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

: 1355670-48-2
(1R,2R,3R,4S,5S)-2-tert-butoxy-1-(hydroxymethyl)spiro[bicyclo[3.1.0]hexane-3,2'-oxiran]-4-ol

Guidance literature:: Multi-step reaction with 4 steps

2.1: 1H-imidazole / dichloromethane / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 1 h / -78 - 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 - 20 °C

4.2: 5 h / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1016/j.tet.2011.11.052