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

Base Information

• Chemical Name: (E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime
• CAS No.: 137759-69-4
• Molecular Formula: C₂₈H₃₇NO₃
• Molecular Weight: 435.607
• Mol file: 137759-69-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime 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) → (E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime (137759-69-4,145313-80-0)

Guidance literature:

Multi-step reaction with 10 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

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

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) → (E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime (137759-69-4,145313-80-0)

Guidance literature:

Multi-step reaction with 14 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

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

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

Reference yield:

[(R)-3,3-Dibromo-1-(2,2-dimethoxy-ethyl)-allyloxymethyl]-benzene (137759-59-2) → (E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal oxime (137759-69-4,145313-80-0)

Guidance literature:

Multi-step reaction with 8 steps

2: over Li-acetylide

3: 49 percent / Swern oxidation

4: Zn(BH₄)2 / diethyl ether

5: LiAlH₄

7: acid, H₂O

8: NH₂OH*HCl, pyridine

With pyridine; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; hydroxylamine hydrochloride; water; In diethyl ether;

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

upstream raw materials:

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

(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:

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

dinoprost

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

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

Refernces