methyl (Z)-7-[(1R,2S,3S,4R)-3-(benzenesulfonamido)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate

Base Information

• Chemical Name: methyl (Z)-7-[(1R,2S,3S,4R)-3-(benzenesulfonamido)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate
• CAS No.: 154634-43-2
• Molecular Formula: C₂₁H₂₉NO₄S
• Molecular Weight: 391.532
• Mol file: 154634-43-2.mol

Synonyms:S-145-Me;154634-43-2

Chemical Property of methyl (Z)-7-[(1R,2S,3S,4R)-3-(benzenesulfonamido)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate

Chemical Property:

• Vapor Pressure: 5.89E-11mmHg at 25°C
• Boiling Point: 521.1°Cat760mmHg
• Flash Point: 268.9°C
• PSA: 80.85000
• Density: 1.21g/cm³
• LogP: 5.14090
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 391.18172958
• Heavy Atom Count: 27
• Complexity: 619

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCC=CCC1C2CCC(C2)C1NS(=O)(=O)C3=CC=CC=C3
• Isomeric SMILES: COC(=O)CCC/C=C\C[C@H]1[C@@H]2CC[C@H](C2)[C@@H]1NS(=O)(=O)C3=CC=CC=C3

Technology Process of methyl (Z)-7-[(1R,2S,3S,4R)-3-(benzenesulfonamido)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate

There total 11 articles about methyl (Z)-7-[(1R,2S,3S,4R)-3-(benzenesulfonamido)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate 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:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-7-((1R,2S,3S,4S)-3-Benzenesulfonylamino-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (154634-43-2)

Guidance literature:

Multi-step reaction with 4 steps

1: dimsylsodium / dimethylsulfoxide

2: diethyl ether

3: various solvent(s)

4: triethylamine / CH₂Cl₂

With dimsylsodium; triethylamine; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm00117a028

Reference yield:

(1S,2S,3S,4R)-3-Allyl-bicyclo[2.2.1]hept-2-ylamine (138258-37-4) → (Z)-7-((1R,2S,3S,4S)-3-Benzenesulfonylamino-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (154634-43-2)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂

2: m-chloroperbenzoic acid / CH₂Cl₂

3: HIO₄ / dioxane; H₂O

4: dimsylsodium / dimethylsulfoxide

5: diethyl ether

6: various solvent(s)

7: triethylamine / CH₂Cl₂

With pyridine; dimsylsodium; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm00117a028

Reference yield:

(+)-exo-3-(2-propenyl)-bicyclo[2.2.1]heptan-2-one (149575-33-7) → (Z)-7-((1R,2S,3S,4S)-3-Benzenesulfonylamino-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (154634-43-2)

Guidance literature:

Multi-step reaction with 9 steps

1: hydroxylamine hydrochloride, KOH / methanol

2: LiAlH₄ / tetrahydrofuran / Heating

3: pyridine / CH₂Cl₂

4: m-chloroperbenzoic acid / CH₂Cl₂

5: HIO₄ / dioxane; H₂O

6: dimsylsodium / dimethylsulfoxide

7: diethyl ether

8: various solvent(s)

9: triethylamine / CH₂Cl₂

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; dimsylsodium; hydroxylamine hydrochloride; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm00117a028

upstream raw materials:

benzenesulfonyl chloride

(4-carboxybutyl)triphenylphosphonium bromide

(1S,2S,3S,4R)-3-Allyl-bicyclo[2.2.1]hept-2-ylamine

(+)-exo-3-(2-propenyl)-bicyclo[2.2.1]heptan-2-one

Downstream raw materials:

Sodium; (Z)-7-((1R,2S,3S,4S)-3-benzenesulfonylamino-bicyclo[2.2.1]hept-2-yl)-hept-5-enoate

Domitroban

Refernces