(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

Base Information

Chemical Name:(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone
CAS No.:1303963-54-3
Molecular Formula:C₁₄H₂₂O₄S
Molecular Weight:286.392
Hs Code.:

Synonyms:(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

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Chemical Property of (R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

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Technology Process of (R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

There total 5 articles about (R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone 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: 77.0%

: 108-94-1,11119-77-0,9003-41-2,9075-99-4
cyclohexanone

: 137909-90-1
1,4-dioxa-8-thiaspiro<4.5>decane-6-carboxaldehyde

: 1303963-54-3
(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

Guidance literature:: cyclohexanone; With water; (R)-5-(pyrrolidin-2-yl)-1H-tetrazole; In dimethyl sulfoxide; at 20 ℃; for 2h;

1,4-dioxa-8-thiaspiro<4.5>decane-6-carboxaldehyde; In dimethyl sulfoxide; for 96h; optical yield given as %ee; enantioselective reaction;
DOI:10.1055/s-0030-1259525

Reference yield:

: 4160-61-6
3-methoxycarbonyltetrahydropyran-4-one

: 1303963-54-3
(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / benzene / 16 h / Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 2 h / -78 - 0 °C / Inert atmosphere

4.1: water; (R)-5-(pyrrolidin-2-yl)-1H-tetrazole / dimethyl sulfoxide / 2 h / 20 °C

4.2: 96 h

With lithium aluminium tetrahydride; oxalyl dichloride; water; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; (R)-5-(pyrrolidin-2-yl)-1H-tetrazole; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1055/s-0030-1259525

Reference yield:

: 4131-74-2
Dimethyl 3,3'-thiodipropionate

: 1303963-54-3
(R)-2-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

2.1: toluene-4-sulfonic acid / benzene / 16 h / Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 2 h / -78 - 0 °C / Inert atmosphere

5.1: water; (R)-5-(pyrrolidin-2-yl)-1H-tetrazole / dimethyl sulfoxide / 2 h / 20 °C

5.2: 96 h

With lithium aluminium tetrahydride; oxalyl dichloride; water; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; (R)-5-(pyrrolidin-2-yl)-1H-tetrazole; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene; 1.1: Dieckmann reaction;
DOI:10.1055/s-0030-1259525