(-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate

Base Information

• Chemical Name: (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate
• CAS No.: 162086-68-2
• Molecular Formula: C₂₁H₃₀O₅S
• Molecular Weight: 394.532
• Mol file: 162086-68-2.mol

Synonyms:(-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate

Chemical Property of (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate

There total 38 articles about (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate 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:

methyl cyclopent-2-ene-1-carboxylate (2258-56-2) → (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.02,6>decan-3-yl p-toluenesulfonate (162086-68-2)

Guidance literature:

Multi-step reaction with 31 steps

1: 92 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / Ambient temperature

2: 92 percent / NaOMe / methanol / 2.5 h / Ambient temperature

3: 10.9 g / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 1N NaOH / methanol / 12 h / Ambient temperature

5: 96 percent / dicyclohexylcarbidiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

6: 25 percent / acetonitrile / 15 °C / Irradiation

7: 1.) DIBAH, 2.) p-toluenesulfonic acid / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temp., 30 min

8: 91 percent / 40percent aq. HF / methanol / 3 h / Ambient temperature

9: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, room temp., 30 min, 2.) MeOH, room temp., 17 h

10: 87 percent / 50percent NaH / dimethylformamide / 1.5 h / Ambient temperature

11: 1.) AcOH, 2.) CrO₃, H₂SO₄ / 1.) THF, water, reflux, 18 h, 2.) acetone, water, room temp., 1 h

12: 2.) pyridinium p-toluenesulfonate / 1.) THF, ether, -78 deg C, 25 min, 2.) CH₂Cl₂, room temp., 16 h

13: DIBAH / toluene; hexane / 1 h / -78 °C

14: 53 percent / 80percent H₂NNH₂*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h

15: 1.) 10percent H₂SO₄, 2.) 15percent NaOH, NaBH₄ / 1.) THF, H₂O, 0 deg C, 30 min, 2.) THF, H₂O, 0 deg C, 1.5 h

16: NaIO₄ / H₂O; ethyl acetate / 2 h / Ambient temperature

17: 30 mg / diethyl ether / 2 h / Ambient temperature

18: CrO₃, H₂SO₄ / acetone; H₂O / 2 h / 0 °C

19: 85 percent / t-BuOK / 2-methyl-propan-2-ol / 0.17 h / 75 °C

20: H₂ / 5percent Pd-C / diethyl ether / 3 h / Ambient temperature

21: 54 percent / 80percent NH₂NH₂*H₂O, KOH / various solvent(s) / 140 deg C, 1.5 h; to 210 deg C, 30 min; 210 deg C, 3.5 h

22: CrO₃, H₂SO₄ / acetone; H₂O / 0.83 h / 0 °C

23: 1.) PhSeCl, 2.) NaHCO₃, NaIO₄ / 1.) AcOEt, room temp., 45 min, 2.) H₂O, MeOH, room temp., 1.5 h

24: DIBAH / diethyl ether; hexane / 0.83 h / -78 °C

25: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, 0 deg C, 5 h, 2.) MeOH, room temp., 13 h

26: 81 percent / 70percent MCPBA / CH₂Cl₂ / 18 h / Ambient temperature

27: pyridinium p-toluenesulfonate / 1 h / Ambient temperature

28: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

29: (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

30: 5percent aq. HCl / CH₂Cl₂

31: pyridine / 69 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; Phenylselenyl chloride; sulfuric acid; hydrogen fluoride; potassium tert-butylate; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; diethylene glycol;

DOI:10.1016/S0040-4020(01)81204-7

Reference yield:

3-hydroxy-cyclopentene-1-carboxylic acid methyl ester (162086-59-1) → (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.02,6>decan-3-yl p-toluenesulfonate (162086-68-2)

Guidance literature:

Multi-step reaction with 29 steps

1: 10.9 g / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 1N NaOH / methanol / 12 h / Ambient temperature

3: 96 percent / dicyclohexylcarbidiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4: 25 percent / acetonitrile / 15 °C / Irradiation

5: 1.) DIBAH, 2.) p-toluenesulfonic acid / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temp., 30 min

6: 91 percent / 40percent aq. HF / methanol / 3 h / Ambient temperature

7: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, room temp., 30 min, 2.) MeOH, room temp., 17 h

8: 87 percent / 50percent NaH / dimethylformamide / 1.5 h / Ambient temperature

9: 1.) AcOH, 2.) CrO₃, H₂SO₄ / 1.) THF, water, reflux, 18 h, 2.) acetone, water, room temp., 1 h

10: 2.) pyridinium p-toluenesulfonate / 1.) THF, ether, -78 deg C, 25 min, 2.) CH₂Cl₂, room temp., 16 h

11: DIBAH / toluene; hexane / 1 h / -78 °C

12: 53 percent / 80percent H₂NNH₂*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h

13: 1.) 10percent H₂SO₄, 2.) 15percent NaOH, NaBH₄ / 1.) THF, H₂O, 0 deg C, 30 min, 2.) THF, H₂O, 0 deg C, 1.5 h

14: NaIO₄ / H₂O; ethyl acetate / 2 h / Ambient temperature

15: 30 mg / diethyl ether / 2 h / Ambient temperature

16: CrO₃, H₂SO₄ / acetone; H₂O / 2 h / 0 °C

17: 85 percent / t-BuOK / 2-methyl-propan-2-ol / 0.17 h / 75 °C

18: H₂ / 5percent Pd-C / diethyl ether / 3 h / Ambient temperature

19: 54 percent / 80percent NH₂NH₂*H₂O, KOH / various solvent(s) / 140 deg C, 1.5 h; to 210 deg C, 30 min; 210 deg C, 3.5 h

20: CrO₃, H₂SO₄ / acetone; H₂O / 0.83 h / 0 °C

21: 1.) PhSeCl, 2.) NaHCO₃, NaIO₄ / 1.) AcOEt, room temp., 45 min, 2.) H₂O, MeOH, room temp., 1.5 h

22: DIBAH / diethyl ether; hexane / 0.83 h / -78 °C

23: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, 0 deg C, 5 h, 2.) MeOH, room temp., 13 h

24: 81 percent / 70percent MCPBA / CH₂Cl₂ / 18 h / Ambient temperature

25: pyridinium p-toluenesulfonate / 1 h / Ambient temperature

26: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

27: (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

28: 5percent aq. HCl / CH₂Cl₂

29: pyridine / 69 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; Phenylselenyl chloride; sulfuric acid; hydrogen fluoride; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; diethylene glycol;

DOI:10.1016/S0040-4020(01)81204-7

Reference yield:

methyl 2,3-epoxycyclopentane-1-carboxylate (162086-60-4,170423-00-4,170423-01-5) → (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.02,6>decan-3-yl p-toluenesulfonate (162086-68-2)

Guidance literature:

Multi-step reaction with 30 steps

1: 92 percent / NaOMe / methanol / 2.5 h / Ambient temperature

2: 10.9 g / imidazole / dimethylformamide / 2 h / Ambient temperature

3: 1N NaOH / methanol / 12 h / Ambient temperature

4: 96 percent / dicyclohexylcarbidiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5: 25 percent / acetonitrile / 15 °C / Irradiation

6: 1.) DIBAH, 2.) p-toluenesulfonic acid / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temp., 30 min

7: 91 percent / 40percent aq. HF / methanol / 3 h / Ambient temperature

8: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, room temp., 30 min, 2.) MeOH, room temp., 17 h

9: 87 percent / 50percent NaH / dimethylformamide / 1.5 h / Ambient temperature

10: 1.) AcOH, 2.) CrO₃, H₂SO₄ / 1.) THF, water, reflux, 18 h, 2.) acetone, water, room temp., 1 h

11: 2.) pyridinium p-toluenesulfonate / 1.) THF, ether, -78 deg C, 25 min, 2.) CH₂Cl₂, room temp., 16 h

12: DIBAH / toluene; hexane / 1 h / -78 °C

13: 53 percent / 80percent H₂NNH₂*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h

14: 1.) 10percent H₂SO₄, 2.) 15percent NaOH, NaBH₄ / 1.) THF, H₂O, 0 deg C, 30 min, 2.) THF, H₂O, 0 deg C, 1.5 h

15: NaIO₄ / H₂O; ethyl acetate / 2 h / Ambient temperature

16: 30 mg / diethyl ether / 2 h / Ambient temperature

17: CrO₃, H₂SO₄ / acetone; H₂O / 2 h / 0 °C

18: 85 percent / t-BuOK / 2-methyl-propan-2-ol / 0.17 h / 75 °C

19: H₂ / 5percent Pd-C / diethyl ether / 3 h / Ambient temperature

20: 54 percent / 80percent NH₂NH₂*H₂O, KOH / various solvent(s) / 140 deg C, 1.5 h; to 210 deg C, 30 min; 210 deg C, 3.5 h

21: CrO₃, H₂SO₄ / acetone; H₂O / 0.83 h / 0 °C

22: 1.) PhSeCl, 2.) NaHCO₃, NaIO₄ / 1.) AcOEt, room temp., 45 min, 2.) H₂O, MeOH, room temp., 1.5 h

23: DIBAH / diethyl ether; hexane / 0.83 h / -78 °C

24: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, 0 deg C, 5 h, 2.) MeOH, room temp., 13 h

25: 81 percent / 70percent MCPBA / CH₂Cl₂ / 18 h / Ambient temperature

26: pyridinium p-toluenesulfonate / 1 h / Ambient temperature

27: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

28: (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

29: 5percent aq. HCl / CH₂Cl₂

30: pyridine / 69 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; Phenylselenyl chloride; sulfuric acid; hydrogen fluoride; potassium tert-butylate; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; diethylene glycol;

DOI:10.1016/S0040-4020(01)81204-7

upstream raw materials:

(-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-ol

p-toluenesulfonyl chloride

methyl cyclopent-2-ene-1-carboxylate

(1S,3aR,3bS,6R,6aR,6bS)-3a,6-Dimethyl-decahydro-cyclobutadicyclopenten-1-ol