(4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole

Base Information

• Chemical Name: (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole
• CAS No.: 137759-49-0
• Molecular Formula: C₂₈H₃₅NO₃
• Molecular Weight: 433.591

Synonyms:(4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole

Chemical Property of (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole

There total 20 articles about (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole 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:

(4R,5R,1'S)-4,5-bis-(1'-hydroxyhex-1'-yl)-2,2-dimethyl-1,3-dioxolane (111846-59-4) → (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole (137759-49-0)

Guidance literature:

Multi-step reaction with 11 steps

2: acid hydrolysis

3: Pb(OAc)4

4: over Li-acetylide

5: 49 percent / Swern oxidation

6: Zn(BH₄)2 / diethyl ether

7: LiAlH₄

9: acid, H₂O

10: NH₂OH*HCl, pyridine

11: 5percent sodium hypochlorite, Et₃N

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; triethylamine; In diethyl ether;

DOI:10.1016/S0040-4039(00)61103-6

Reference yield:

(4R,5R)-4,5-Bis-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane (137759-54-7) → (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole (137759-49-0)

Guidance literature:

Multi-step reaction with 16 steps

1: p-TsOH / methanol

2: acetylation

3: 1) O₃, 2) Me₂S / 1) MeOH, -78 deg C

4: p-TsOH

5: K₂CO₃ / methanol

6: 96 percent / Pb(OAc)4, K₂CO₃ / benzene

7: 58 percent / PPh₄

9: over Li-acetylide

10: 49 percent / Swern oxidation

11: Zn(BH₄)2 / diethyl ether

12: LiAlH₄

14: acid, H₂O

15: NH₂OH*HCl, pyridine

16: 5percent sodium hypochlorite, Et₃N

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; dimethylsulfide; hydroxylamine hydrochloride; water; tetraphenylphosphonium; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; In methanol; diethyl ether; benzene;

DOI:10.1016/S0040-4039(00)61103-6

Reference yield:

(4R,5S,6S,7R)-4,7-bis(benzyloxy)deca-1,9-diene-5,6-diol (145308-09-4) → (4R,5R)-5-Benzyloxy-4-((E)-(S)-3-benzyloxy-oct-1-enyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazole (137759-49-0)

Guidance literature:

Multi-step reaction with 15 steps

1: acetylation

2: 1) O₃, 2) Me₂S / 1) MeOH, -78 deg C

3: p-TsOH

4: K₂CO₃ / methanol

5: 96 percent / Pb(OAc)4, K₂CO₃ / benzene

6: 58 percent / PPh₄

8: over Li-acetylide

9: 49 percent / Swern oxidation

10: Zn(BH₄)2 / diethyl ether

11: LiAlH₄

13: acid, H₂O

14: NH₂OH*HCl, pyridine

15: 5percent sodium hypochlorite, Et₃N

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; dimethylsulfide; hydroxylamine hydrochloride; water; tetraphenylphosphonium; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; In methanol; diethyl ether; benzene;

DOI:10.1016/S0040-4039(00)61103-6

upstream raw materials:

(E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime

(4R,5R,1'S)-4,5-bis-(1'-hydroxyhex-1'-yl)-2,2-dimethyl-1,3-dioxolane

[(R)-3,3-Dibromo-1-(2,2-dimethoxy-ethyl)-allyloxymethyl]-benzene

(4R,5S,6S,7R)-4,7-bis(benzyloxy)deca-1,9-diene-5,6-diol

Downstream raw materials:

dinoprost

(3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone

(2R,3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-((Z)-7-hydroxy-hept-2-enyl)-cyclopentanone

(Z)-7-[(1R,2R,3R,5S)-3-Benzyloxy-2-((E)-(S)-3-benzyloxy-oct-1-enyl)-5-hydroxy-cyclopentyl]-hept-5-enoic acid

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