(16R)-17-Hydroxysarpagane-16-carboxylic acid methyl ester

Base Information

• Chemical Name: (16R)-17-Hydroxysarpagane-16-carboxylic acid methyl ester
• CAS No.: 6872-44-2
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 6872-44-2.mol

Synonyms:3-ethylidene-13-hydroxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester;(16R)-17-hydroxysarpagan-16-carboxylic acid methyl ester;(+)-polyneuridine;

Chemical Property of (16R)-17-Hydroxysarpagane-16-carboxylic acid methyl ester

Chemical Property:

• Melting Point: 231-3°C
• PSA: 65.56000
• LogP: 2.50510

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This carboline alkaloid from Aspidosperma polyneuron crystallizes from EtOH as the solvate with m.p. 245-247.5°C; [α]D - 68° (c 0.67, pyridine) and from C6H6 as the solvate, m.p. 243-6°C; [α]D + 1° (CHCI3) or - 73° (c 0.82, pyridine). The ultraviolet spectrum in EtOH has absorption maxima at 228 and 281 mJ.1, while that in acidic solution (EtOH-HCl) has maxima at 221" and 273 mJ.1. The methiodide has m.p. 263-5°C and the O-acetate, m.p. 27)-2°C; [α]D - 92° (c 0.71, pyridine). Oxidation with chromic acid yields the corresponding aldehyde, m.p. 285'--6°C. Reduction with LiAIH4 gives the diol, m.p. 260-5°C; [α]D - 36° (c 1.05, pyridine) or - 14° (c 1.1, MeOH).

Technology Process of (16R)-17-Hydroxysarpagane-16-carboxylic acid methyl ester

There total 2 articles about (16R)-17-Hydroxysarpagane-16-carboxylic 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:

→ 17-hydroxy-sarpagane-16-carboxylic acid methyl ester (639-36-1,6872-44-2,113973-31-2)

Guidance literature:

Aldehyd (II), NaBH4;

DOI:10.1007/BF00568730

Reference yield:

Polyneuridine aldehyde (2520-44-7,92218-35-4) → akuammidine (639-36-1,6872-44-2,113973-31-2)

Guidance literature:

With NADPH; Vellosimine reductase;

DOI:10.1016/S0040-4020(01)91118-4

Reference yield: 75.0%

(16R)-17-hydroxysarpagan-16-carboxylic acid methyl ester (6872-44-2) → (+)-polyneuridine aldehyde (2520-44-7)

Guidance literature:

With N-chloro-succinimide; dimethylsulfide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol062762q

upstream raw materials:

Polyneuridine aldehyde

Downstream raw materials:

(2S,6S,13S)-3-Eth-(E)-ylidene-13-formyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester

(+)-polyneuridine aldehyde

vellosimine

Refernces