Cyclopentanone, 2-(hydroxymethyl)-4-(phenylmethoxy)-3-[3-(phenylmethoxy)-1-octenyl]-

Base Information

• Chemical Name: Cyclopentanone, 2-(hydroxymethyl)-4-(phenylmethoxy)-3-[3-(phenylmethoxy)-1-octenyl]-
• CAS No.: 137759-70-7
• Molecular Formula: C28H36O4
• Molecular Weight: 436.591
• Mol file: 137759-70-7.mol

Synonyms:

Chemical Property of Cyclopentanone, 2-(hydroxymethyl)-4-(phenylmethoxy)-3-[3-(phenylmethoxy)-1-octenyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanone, 2-(hydroxymethyl)-4-(phenylmethoxy)-3-[3-(phenylmethoxy)-1-octenyl]-

There total 18 articles about Cyclopentanone, 2-(hydroxymethyl)-4-(phenylmethoxy)-3-[3-(phenylmethoxy)-1-octenyl]- 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) → (3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-hydroxymethyl-cyclopentanone (137759-70-7)

Guidance literature:

Multi-step reaction with 12 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

12: H₂, boric acid / W-2 Raney nickel

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; hydrogen; boric acid; triethylamine; W-2 Raney nickel; 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) → (3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-hydroxymethyl-cyclopentanone (137759-70-7)

Guidance literature:

Multi-step reaction with 17 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

17: H₂, boric acid / W-2 Raney nickel

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; dimethylsulfide; hydroxylamine hydrochloride; water; hydrogen; boric acid; tetraphenylphosphonium; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; W-2 Raney nickel; In methanol; diethyl ether; benzene;

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

Reference yield:

(6S,7S,8S,9S)-6,9-Bis-benzyloxy-tetradecane-7,8-diol (133963-39-0) → (3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-hydroxymethyl-cyclopentanone (137759-70-7)

Guidance literature:

Multi-step reaction with 10 steps

1: Pb(OAc)4

2: over Li-acetylide

3: 49 percent / Swern oxidation

4: Zn(BH₄)2 / diethyl ether

5: LiAlH₄

7: acid, H₂O

8: NH₂OH*HCl, pyridine

9: 5percent sodium hypochlorite, Et₃N

10: H₂, boric acid / W-2 Raney nickel

With pyridine; lead(IV) acetate; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; hydrogen; boric acid; triethylamine; W-2 Raney nickel; In diethyl ether;

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

upstream raw materials:

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

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

(4R,5R)-4,5-Bis-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane

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

Downstream raw materials:

dinoprost

(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

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

Refernces