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

Base Information

Chemical Name:(3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone
CAS No.:137759-71-8
Molecular Formula:C₂₈H₃₄O₃
Molecular Weight:418.576
Hs Code.:

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

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

Chemical Property:

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

There total 20 articles about (3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone 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:

: 111846-59-4
(4R,5R,1'S)-4,5-bis-(1'-hydroxyhex-1'-yl)-2,2-dimethyl-1,3-dioxolane

: 137759-71-8
(3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone

Guidance literature:: Multi-step reaction with 13 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

13: MsCl, DMAP

With pyridine; lead(IV) acetate; dmap; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; hydrogen; boric acid; methanesulfonyl chloride; triethylamine; W-2 Raney nickel; In diethyl ether;
DOI:10.1016/S0040-4039(00)61103-6

Reference yield:

: 137759-54-7
(4R,5R)-4,5-Bis-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane

: 137759-71-8
(3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone

Guidance literature:: Multi-step reaction with 18 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

18: MsCl, DMAP

With pyridine; lead(IV) acetate; dmap; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; dimethylsulfide; hydroxylamine hydrochloride; water; hydrogen; boric acid; tetraphenylphosphonium; potassium carbonate; toluene-4-sulfonic acid; ozone; methanesulfonyl chloride; triethylamine; W-2 Raney nickel; In methanol; diethyl ether; benzene;
DOI:10.1016/S0040-4039(00)61103-6

Reference yield:

: 133963-39-0
(6S,7S,8S,9S)-6,9-Bis-benzyloxy-tetradecane-7,8-diol

: 137759-71-8
(3R,4R)-4-Benzyloxy-3-((E)-(S)-3-benzyloxy-oct-1-enyl)-2-methylene-cyclopentanone

Guidance literature:: Multi-step reaction with 11 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

11: MsCl, DMAP

With pyridine; lead(IV) acetate; dmap; sodium hypochlorite; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; hydrogen; boric acid; methanesulfonyl chloride; triethylamine; W-2 Raney nickel; In diethyl ether;
DOI:10.1016/S0040-4039(00)61103-6