8,9-Dehydro-9,6-nitrilo-7-thia-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether

Base Information

• Chemical Name: 8,9-Dehydro-9,6-nitrilo-7-thia-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether
• CAS No.: 82945-89-9
• Molecular Formula: C₃₆H₄₇NO₆S
• Molecular Weight: 621.838

Synonyms:

Chemical Property of 8,9-Dehydro-9,6-nitrilo-7-thia-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 8,9-Dehydro-9,6-nitrilo-7-thia-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether

There total 15 articles about 8,9-Dehydro-9,6-nitrilo-7-thia-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether 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:

5-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-pentanoic acid methyl ester (85250-50-6,85281-50-1) → 5-[(5S,6R)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-5,6-dihydro-4H-cyclopentathiazol-2-yl]-pentanoic acid methyl ester (82945-89-9,82978-17-4)

Guidance literature:

With Ph₃P-diethyl azodicarboxylate; In tetrahydrofuran; at 25 ℃; Yield given;

DOI:10.1016/S0040-4039(00)87097-5

Reference yield:

5-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-pentanoic acid methyl ester (85250-50-6,85281-50-1) → 5-[(5S,6R)-5-Benzyloxymethoxy-6-((E)-(S)-3-benzyloxymethoxy-oct-1-enyl)-5,6-dihydro-4H-cyclopentathiazol-2-yl]-pentanoic acid methyl ester (82978-17-4) + 8,9-Dehydro-9,6-nitrilo-7-thia-PGF1 methyl ester 11,15-bis<(phenylmethoxy)methyl>ether (82945-89-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Title compound not separated from byproducts; 1.) 0 deg C, 2.) 25 deg C, 20 h;

DOI:10.1021/jo00158a031

Reference yield:

6-oxabicyclo[3.1.0]hex-2-ene (7129-41-1) → 5-[(5S,6R)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-5,6-dihydro-4H-cyclopentathiazol-2-yl]-pentanoic acid methyl ester (82945-89-9,82978-17-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 29 percent

2: p-TsOH / methanol / 25 °C

3: LiAlH₄ / tetrahydrofuran / Heating

4: 77 percent / Pr₂NEt / 25 °C

5: 57 percent / N-bromosuccinimide, H₂O / dimethylsulfoxide

6: 94 percent / pyridinium chlorochromate / CH₂Cl₂

7: neat (no solvent) / Ambient temperature

8: complex of triphenyl phosphine and diethyl azodicarboxylate / tetrahydrofuran / 25 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; dipropylethylamine; Ph₃P-diethyl azodicarboxylate; water; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)87097-5

upstream raw materials:

5-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-pentanoic acid methyl ester

6-oxabicyclo[3.1.0]hex-2-ene

methyl 6-amino-6-oxohexanoate

3-(α-Ethoxy)-ethoxy-1-lithio-1-octin

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