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

Base Information

• Chemical Name: 4-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-butyric acid methyl ester
• CAS No.: 85250-51-7
• Molecular Formula: C₃₅H₄₇NO₇S
• Molecular Weight: 625.827

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 4-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-butyric acid methyl ester 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:

6-oxabicyclo[3.1.0]hex-2-ene (7129-41-1) → 4-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-butyric acid methyl ester (85250-51-7,85281-51-2)

Guidance literature:

Multi-step reaction with 7 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

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

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

Reference yield:

methyl 5-amino-5-oxopentanoate (102040-91-5) → 4-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-butyric acid methyl ester (85250-51-7,85281-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: P₂O₁₀

2: neat (no solvent) / Ambient temperature

With P₂O₁₀; In neat (no solvent);

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

Reference yield:

3-(α-Ethoxy)-ethoxy-1-lithio-1-octin (53398-57-5) → 4-[(3aS,5S,6R,6aS)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-3a-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentathiazol-2-yl]-butyric acid methyl ester (85250-51-7,85281-51-2)

Guidance literature:

Multi-step reaction with 7 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

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

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

upstream raw materials:

4-Thiocarbamoyl-butyric acid methyl ester

(3S,4R)-4-Benzyloxymethoxy-3-((E)-3-benzyloxymethoxy-oct-1-enyl)-2-bromo-cyclopentanone

6-oxabicyclo[3.1.0]hex-2-ene

methyl 5-amino-5-oxopentanoate

Downstream raw materials:

4-[(5S,6R)-5-Benzyloxymethoxy-6-((E)-(S)-3-benzyloxymethoxy-oct-1-enyl)-5,6-dihydro-4H-cyclopentathiazol-2-yl]-butyric acid methyl ester

8,9-Dehydro-9,6-nitrilo-7-thia-2-nor-PGF₁ methyl ester 11,15-bis<(phenylmethoxy)methyl>ether

4-[(5S,6R)-5-Benzyloxymethoxy-6-((E)-3-benzyloxymethoxy-oct-1-enyl)-5,6-dihydro-4H-cyclopentathiazol-2-yl]-butyric acid methyl ester

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