(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Base Information

• Chemical Name: (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one
• CAS No.: 1446428-36-9
• Molecular Formula: C₂₀H₃₆O₂S₂Si
• Molecular Weight: 400.722

Synonyms:(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Chemical Property of (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Chemical Property:

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Technology Process of (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

There total 4 articles about (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one 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: 68.0%

carbon disulfide (75-15-0,12122-00-8) + (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one (131691-33-3) + 1,3-dibromo-propane (109-64-8) → (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one (1446428-36-9)

Guidance literature:

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

carbon disulfide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -78 - 0 ℃; for 2.5h; Inert atmosphere;

1,3-dibromo-propane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere; Enzymatic reaction;

DOI:10.1016/j.tet.2013.05.082

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one (1446428-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere

2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 2.5 h / -78 - 0 °C / Inert atmosphere

3.3: 0 - 20 °C / Inert atmosphere; Enzymatic reaction

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1016/j.tet.2013.05.082

Reference yield:

(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2) → (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one (1446428-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 2.5 h / -78 - 0 °C / Inert atmosphere

2.3: 0 - 20 °C / Inert atmosphere; Enzymatic reaction

With oxalyl dichloride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;

DOI:10.1016/j.tet.2013.05.082

upstream raw materials:

(1R,2S,5R)-2-[2'-hydroxy-10-methylethyl]-5-methylcyclohexan-1-ol

tert-butyldimethylsilyl chloride

carbon disulfide

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one

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