ent-Corey PG-Lactone Diol

Base Information

• Chemical Name: ent-Corey PG-Lactone Diol
• CAS No.: 53110-06-8
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.353
• Mol file: 53110-06-8.mol

Synonyms:

Chemical Property of ent-Corey PG-Lactone Diol

Chemical Property:

• Boiling Point: 430.1±45.0 °C(Predicted)
• PKA: 14.30±0.40(Predicted)
• Density: 1.199±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

ent-Corey PG-Lactone Diol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Corey prostaglandin (PG)-lactone diol is a versatile, chiral intermediate used in the preparation of PGs and PG analogs. ent-Corey PG-lactone diol is the opposite enantiomer of corey PG-lactone diol.

Technology Process of ent-Corey PG-Lactone Diol

There total 49 articles about ent-Corey PG-Lactone Diol 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: 80.8%

lactone of 5α-hydroxy-3α-(2-tetrahydrofuryloxy)-2β-<3α-(2-tetrahydrofuryloxy)-trans-1-octenyl>cyclopentyl-1α-acetic acid (114951-80-3) → (1SR,5RS,6RS,7RS)-7-hydroxy-6-<(3SR)-3-hydroxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one (23782-33-4,26054-67-1,39182-59-7,39521-48-7,39648-33-4,39648-34-5,42586-67-4,42586-74-3,52992-73-1,53110-06-8,53275-56-2,54383-09-4,58865-62-6,58865-63-7,62929-80-0,62929-81-1,67179-95-7)

Guidance literature:

With Dowex 50 x 2 (H⁽¹⁺⁾) ion-exchange resin; In ethanol; for 1h; Ambient temperature;

Reference yield:

trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone (78823-20-8) → (3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (23782-33-4,26054-67-1,39182-59-7,39521-48-7,39648-33-4,39648-34-5,42586-67-4,42586-74-3,52992-73-1,53110-06-8,53275-56-2,54383-09-4,58865-62-6,58865-63-7,62929-80-0,62929-81-1,67179-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1. LDA / 1. THF, -78 deg C;

2: 1. LiAlH₄, 2. i-Pr₂EtN / 1. Et₂O, 2. CH₂Cl₂

3: 70 percent / CuSO₄ / benzene / 90 °C

4: 95 percent / Et₃NF / tetrahydrofuran / Ambient temperature

5: 80 percent / Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride (PBPH) / tetrahydrofuran / a. -78 deg C, b. RT

6: 15percent aq. HF / acetonitrile

7: 5percent HCl / tetrahydrofuran; H₂O

With hydrogenchloride; lithium aluminium tetrahydride; Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride; hydrogen fluoride; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; copper(II) sulfate; In tetrahydrofuran; water; acetonitrile; benzene;

DOI:10.1021/jo00200a063

Reference yield:

trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene (93566-56-4,93711-56-9,110548-21-5) → (3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (23782-33-4,26054-67-1,39182-59-7,39521-48-7,39648-33-4,39648-34-5,42586-67-4,42586-74-3,52992-73-1,53110-06-8,53275-56-2,54383-09-4,58865-62-6,58865-63-7,62929-80-0,62929-81-1,67179-95-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1. LiAlH₄, 2. i-Pr₂EtN / 1. Et₂O, 2. CH₂Cl₂

2: 70 percent / CuSO₄ / benzene / 90 °C

3: 95 percent / Et₃NF / tetrahydrofuran / Ambient temperature

4: 80 percent / Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride (PBPH) / tetrahydrofuran / a. -78 deg C, b. RT

5: 15percent aq. HF / acetonitrile

6: 5percent HCl / tetrahydrofuran; H₂O

With hydrogenchloride; lithium aluminium tetrahydride; Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride; hydrogen fluoride; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; copper(II) sulfate; In tetrahydrofuran; water; acetonitrile; benzene;

DOI:10.1021/jo00200a063

upstream raw materials:

(1SR,5RS,6RS,7RS)-7-acetoxy-6-<3-acetoxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one

3aα,6aα-4β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-5α-(methoxymethoxy)perhydropentafuran-2-one

(1α,5α)-3β-hydroxy-2α-<(E)-(3S^*)-3-hydroxyoct-1-enyl>bicyclo<3.2.0>heptan-6-one

γ-lactone of 2β-(3-oxo-trans-1-octenyl)-3α-hydroxy-5α-hydroxy-1α-cyclopentylacetic acid

Downstream raw materials:

(3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-trimethylsilanylethynyl-hexahydro-cyclopenta[b]pyrrol-2-one

(3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-prop-1-ynyl-hexahydro-cyclopenta[b]pyrrol-2-one

(3aR,4R,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-6a-phenylsulfanyl-hexahydro-cyclopenta[b]pyrrol-2-one

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