6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane

Base Information

• Chemical Name: 6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane
• CAS No.: 119245-37-3
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488

Synonyms:6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane

Chemical Property of 6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane

There total 5 articles about 6(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane 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: 76.0%

6(R*)-<2(R*)-hydroxycyclohex-1(S*)-yl>-10(S*)-<2(S*)-<(phenylmethyl)oxy>cyclohex-1(R*)-yl>-1,4-dioxaspiro<4.5>decane (119245-34-0) → 6(R*)-(2(R*)-hydroxycyclohex-1(S*)-yl)-10(S*)-(2(S*)-hydroxycyclohex-1(R*)-yl)-1,4-dioxaspiro<4.5>decane (119245-37-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol; for 9h;

DOI:10.1021/jo00269a042

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 6(R*)-(2(R*)-hydroxycyclohex-1(S*)-yl)-10(S*)-(2(S*)-hydroxycyclohex-1(R*)-yl)-1,4-dioxaspiro<4.5>decane (119245-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) KOH, 2.) p-toluenesulfonic acid / 1.) toluene, 190 deg C, 6.5 h, 2.) reflux, 3 d

2: 1.) thexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, 6.8 h, 2.) ethanol, 45-50 deg C, 75 min

3: 1.) 1,10-phenanthroline, ethylmagnesium bromide / 1.) THF, HMPA, ether, 0 deg C, 45 min, 2.) 80 deg C

4: 1.) thexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, overnight, 2.) ethanol, 45-50 deg C, 3.3 h

5: 76 percent / H₂ / 5percent Pd/C / propan-2-ol / 9 h

With potassium hydroxide; sodium hydroxide; 1,10-Phenanthroline; thexylborane; ethylmagnesium bromide; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1021/jo00269a042

Reference yield:

6(R*),10(S*)-di(1-cyclohexen-1-yl)-1,4-dioxaspiro<4.5>decane (119245-30-6) → 6(R*)-(2(R*)-hydroxycyclohex-1(S*)-yl)-10(S*)-(2(S*)-hydroxycyclohex-1(R*)-yl)-1,4-dioxaspiro<4.5>decane (119245-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) thexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, 6.8 h, 2.) ethanol, 45-50 deg C, 75 min

2: 1.) 1,10-phenanthroline, ethylmagnesium bromide / 1.) THF, HMPA, ether, 0 deg C, 45 min, 2.) 80 deg C

3: 1.) thexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, overnight, 2.) ethanol, 45-50 deg C, 3.3 h

4: 76 percent / H₂ / 5percent Pd/C / propan-2-ol / 9 h

With sodium hydroxide; 1,10-Phenanthroline; thexylborane; ethylmagnesium bromide; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1021/jo00269a042

upstream raw materials:

6(R^*)-<2(R^*)-hydroxycyclohex-1(S^*)-yl>-10(S^*)-<2(S^*)-<(phenylmethyl)oxy>cyclohex-1(R^*)-yl>-1,4-dioxaspiro<4.5>decane

cyclohexanone

6(R^*),10(S^*)-di(1-cyclohexen-1-yl)-1,4-dioxaspiro<4.5>decane

6(R^*)-(1-cyclohexen-1-yl)-10(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)-1,4-dioxaspiro<4.5>decane

Downstream raw materials:

C₁₈H₂₈O₂

2(R^*)-(2(R^*)-hydroxycyclohex-1(S^*)-yl)-6(S^*)-(2(S^*)-hydroxycyclohex-1(R^*)-yl)cyclohexanone

6(R^*)-<2-oxycyclohex-1(S^*)-yl>-10(S^*)-<2-oxycyclohex-1(R^*)-yl>-1,4-dioxaspiro<4.5>decane

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