(1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol

Base Information

• Chemical Name: (1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol
• CAS No.: 85737-84-4
• Molecular Formula: C₁₁H₁₇BrO₃
• Molecular Weight: 277.158
• Mol file: 85737-84-4.mol

Synonyms:(1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol

Chemical Property of (1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol

There total 1 articles about (1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.0^3,8]undecan-6-ol 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:

methanol (67-56-1) + (1R,4S,4aR,8aS)-4-(acetoxy)-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl acetate (85737-81-1,115333-86-3) → (1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.03,8]undecan-6-ol (85737-84-4)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)85878-5

Reference yield:

(1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.03,8]undecan-6-ol (85737-84-4) → (+/-)-Compactin (73573-88-3,84173-29-5,84173-30-8,84173-31-9,85798-43-2,109785-28-6,109785-29-7,125133-73-5,58948-09-7)

Guidance literature:

Multi-step reaction with 17 steps

1: N,N-Diisopropylethylamine / CH₂Cl₂

2: KOCMe₃ / dimethylsulfoxide / 25 °C

3: 1.) KOCMe₃ 2.) CH₃SO₂Cl, pyridine / 0 - 80 °C

4: 1.) LDA / 1.) THF, -78 deg C 2.) -78 to -35 deg C

5: aq. HCl / tetrahydrofuran / 60 °C

7: 98 percent / pyridine / tetrahydrofuran / 25 °C

8: 80 percent / tetrahydrofuran / 0 °C

9: 82 percent / aq. HCl / tetrahydrofuran / 0 °C

10: Hydrogen / (Ph₃P)3RhCl / toluene / 25 °C

11: 1N aq. NaOH / methanol / 25 °C

12: 75 percent / 10percent aq. HCl / CH₂Cl₂ / 25 °C

13: DIBAL / toluene / -78 °C

14: 35 percent / tetrahydrofuran / 25 °C

15: DMAP / pyridine / 25 °C

16: 1.) 9BBN 2.) H₂O₂

With pyridine; hydrogenchloride; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; Wilkinson's catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4039(00)94509-X

Reference yield:

(1R,3S,6R,7S,8R)-10-Bromo-1-methoxy-2-oxa-tricyclo[5.3.1.03,8]undecan-6-ol (85737-84-4) → (+/-) compactin (73573-88-3,84173-29-5,84173-30-8,84173-31-9,85798-43-2,109785-28-6,109785-29-7,125133-73-5,58948-09-7)

Guidance literature:

Multi-step reaction with 16 steps

1: KOBu^t / dimethylsulfoxide / 25 °C

2: pyridine / 0 °C

4: PCC / CH₂Cl₂

5: tetrahydrofuran / 25 °C

6: Catecholborane

7: 95 percent / 2,4,4,6-tetrabromocyclohexadienone / CH₂Cl₂

8: 94 percent / Zn, 2-propanol, HOAc / 85 °C

9: 100 percent / pyridine, DMAP / 25 °C

10: 1.) 9BBN, H₂O₂, 2.) imid / 2.) DMF

11: 95 percent / K₂CO₃, aq. CH₃OH / 25 °C

13: 75 percent / CrO₃, pyridine / CH₂Cl₂

14: 1.) TiCl₄ / 1.) -78 deg C

15: NaBH₄ / methanol / 0 °C

16: 1.) K₂CO₃, 2.) 10percent HCl-CH₂CL₂ / 1.) aq CH₃OH, 25 deg C, 2.) CH₂Cl₂

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; potassium tert-butylate; dihydrogen peroxide; titanium tetrachloride; potassium carbonate; acetic acid; isopropyl alcohol; pyridinium chlorochromate; zinc; benzo[1,3,2]dioxaborole; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)85878-5

upstream raw materials:

methanol

(1R,4S,4aR,8aS)-4-(acetoxy)-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl acetate

Downstream raw materials:

3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

C₂₄H₃₂N₂O₅S

(+/-) compactin

(+/-)-Compactin