Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Base Information

• Chemical Name: Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• CAS No.: 6474-90-4
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.433
• European Community (EC) Number: 229-331-0
• Wikidata: Q27166938
• Mol file: 6474-90-4.mol

Synonyms:6474-90-4;Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate;C21H24N2O3;Prestwick_462;Prestwick0_000593;Prestwick1_000593;Prestwick2_000593;SPBio_002685;SCHEMBL14095094;CHEBI:95146;HMS1569H08;LSM-6418;MFCD31745763;AKOS032948288;Alstonine, 3,4,5,6-tetrahydro-, (3..)-;Q27166938;(4S,4aS,14aS)-methyl 4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate

Chemical Property of Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Chemical Property:

• Melting Point: 227 °C
• Boiling Point: 524 °C at 760 mmHg
• PKA: 18.03±0.60(Predicted)
• Flash Point: 270.7 °C
• PSA: 54.56000
• Density: 1.3 g/cm³
• LogP: 3.11670
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 606

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetrahydroalstonine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45
• Isomeric SMILES: C[C@H]1[C@@H]2CN3CCC4=C(C3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

Technology Process of Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

There total 107 articles about Methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate 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: 80.6%

strictosidine (19456-89-4,20824-29-7) → tetrahydroalstonine (6474-90-4)

Guidance literature:

strictosidine; With β-glucosidase; at 37 ℃; for 24h; pH=5; aq. acetate buffer; Inert atmosphere; Enzymatic reaction;

With sodium tetrahydroborate; acetic acid; regioselective reaction; Inert atmosphere;

DOI:10.1002/asia.201000520

Reference yield: 41.0%

2,3-seco-2,3-dihydroakuammigine (51020-37-2) → tetrahydroalstonine (6474-90-4)

Guidance literature:

2,3-seco-2,3-dihydroakuammigine; With mercury(II) diacetate; edetate disodium; acetic acid; In water; at 80 ℃; for 4.5h; Inert atmosphere;

With sodium tetrahydroborate; sodium hydroxide; In methanol; water; at 0 ℃; for 0.333333h; pH=9; Inert atmosphere;

Reference yield: 40.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + 2-deoxoisopteropodine (83541-47-3) → N(a)-methylthiomethyl-2-deoxoisopteropodine (83482-71-7) + tetrahydroalstonine (6474-90-4) + akuammigine (642-17-1)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; for 1h; temperature: allowed to warm from -78 deg C;

upstream raw materials:

tryptamine

(4S)-5c-formyl-4r-methoxycarbonylmethyl-6t-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

(4aS)-7-(2-indol-3-yl-ethyl)-1c-methyl-6-oxo-(4ar,8ac)-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester

alstonine

Downstream raw materials:

tetrahydroalstonine

19α-methyl-(20α)-18-oxa-yohimb-16-ene-16-carboxylic acid

isopteropodine

ajmalicine

Refernces

• 1、 Schlittler et al.. "-". . p. 271,273. Retrieved 1952.
• 2、 -. "ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES". . . Retrieved 2016/11/21.
• 3、 Stoeckigt, Joachim,Hammes, Bodo,Ruppert, Martin. "Construction and expression of a dual vector for chemo-enzymatic synthesis of plant indole alkaloids in Escherichia coli". scheme or table. p. 759 - 766. Retrieved 2010/09/07.