<6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate

Base Information

• Chemical Name: <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate
• CAS No.: 185515-97-3
• Molecular Formula: C₃₄H₅₃NO₇Si
• Molecular Weight: 615.883

Synonyms:<6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate

Chemical Property of <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate

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Technology Process of <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate

There total 7 articles about <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate 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: 100.0%

t-butyldimethylsiyl triflate (69739-34-0) + <6S-<6α,7β,(1S*,2R*,5S*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate (185515-96-2) → <6S-<6α,7β,(1S*,2R*,5S*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate (185515-97-3)

Guidance literature:

With 2,6-dimethylpyridine;

DOI:10.1039/CC9960002543

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → <6S-<6α,7β,(1S*,2R*,5S*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate (185515-97-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 0.08 h / 0 °C

2: 100 percent / aq. NaIO₄, OsO₄ / dioxane / 2 h

3: 91 percent / neutral alumina / 1.) 0 deg C, 0.5 h, 2.) r.t., 3 h

4: 90 percent / MsCl, Et₃N / 0.12 h / 0 °C

5: 2.) aq. NH₄Cl / 1.) THF, -78 deg C, 35 min, 2.) r.t., 2 h

6: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C

7: 100 percent / 2,6-lutidine

With 2,6-dimethylpyridine; dmap; aluminum oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ammonium chloride; methanesulfonyl chloride; triethylamine; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1039/CC9960002543

Reference yield:

(1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → <6S-<6α,7β,(1S*,2R*,5S*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate (185515-97-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / neutral alumina / 1.) 0 deg C, 0.5 h, 2.) r.t., 3 h

2: 90 percent / MsCl, Et₃N / 0.12 h / 0 °C

3: 2.) aq. NH₄Cl / 1.) THF, -78 deg C, 35 min, 2.) r.t., 2 h

4: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C

5: 100 percent / 2,6-lutidine

With 2,6-dimethylpyridine; aluminum oxide; sodium tetrahydroborate; ammonium chloride; methanesulfonyl chloride; triethylamine; In methanol;

DOI:10.1039/CC9960002543

upstream raw materials:

t-butyldimethylsiyl triflate

<6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate

(-)-8-phenylmenthol

(1R,3R,4S)-8-phenylmenthyl glyoxylate

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