Collettiside I

Base Information

• Chemical Name: Collettiside I
• CAS No.: 14144-06-0
• Molecular Formula: C33H52O8
• Molecular Weight: 576.771
• DSSTox Substance ID: DTXSID90864471
• Metabolomics Workbench ID: 35180
• Wikidata: Q105314746
• Mol file: 14144-06-0.mol

Synonyms:Collettiside I;Melongoside B;Funkioside A;diosgenin 3-O-beta-D-glucopyranoside;Alliumoside A?;Disogluside, INN;DTXSID90864471;Spirost-5-en-3-yl hexopyranoside;WA 185

Chemical Property of Collettiside I

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 275～280℃
• Refractive Index: 1.594
• Boiling Point: 705.1 °C at 760 mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 380.2 °C
• PSA: 117.84000
• Density: 1.278 g/cm³
• LogP: 3.53810
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 576.36621861
• Heavy Atom Count: 41
• Complexity: 1030

Purity/Quality:

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

Diosgenin?glucoside 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)O)C)C)C)OC1

Technology Process of Collettiside I

There total 40 articles about Collettiside I 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: 100.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) + diosgenin (512-04-9) → trillin (14144-06-0)

Guidance literature:

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate; diosgenin; With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 0.25h;

With sodium methylate;

DOI:10.1021/jo990603x

Reference yield: 99.0%

diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside (120969-06-4) → trillin (14144-06-0)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03038

Reference yield: 89.0%

maltodextrin + diosgenin (512-04-9) → trillin (14144-06-0)

Guidance literature:

With glucose-1-phosphate thymidylyltransferase from Escherichia coli K₁₂; inorganic pyrophosphatase from Escherichia coli K₁₂; maltodextrin phosphorylase from Escherichia coli K₁₂; solanidine glucosyltransferase from Solanum tuberosum; UTP; magnesium chloride; at 40 ℃; for 48h; pH=9; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.tetlet.2010.01.077

upstream raw materials:

(3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside

(3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside

diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside

(25R)-3β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-spirost-5-ene

Downstream raw materials:

diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside

diosgenyl 6-O-p-toluenesulfonyl-β-D-glucopyranoside

dioscin

diosgenyl 3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside

Refernces

• 1、 Ma, James C. N.,Lau, F. W.. "STRUCTURE CHARACTERIZATION OF HAEMOSTATIC DIOSGENIN GLYCOSIDES FROM PARIS POLYPHYLLA". . p. 1561 - 1566. Retrieved 1985.
• 2、 Espejo,O.,Llavot,J.. "-". . p. 413. Retrieved 1982.
• 3、 Marker,Krueger. "-". . p. 2548. Retrieved 1940.
• 4、 Kim, Dong-Hwan,Hong, Bin Na,Le, Hoa Thi,Hong, Ha Na,Lim, Choon Woo,Park, Keun Ha,Kim, Tae Woo,Kang, Tong Ho. "Small molecular weight PEGylation of diosgenin in an in vivo animal study for diabetic auditory impairment treatment". . p. 4609 - 4612. Retrieved 2012.
• 5、 Huang, Hongzhi,Zhao, Min,Lu, Li,Tan, Dawei,Zhou, Wenbin,Xiong, Chengqi,Zhao, Yang,Song, Xinbo,Yu, Liyan,Ma, Baiping. "Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin". . p. 1 - 7. Retrieved 2013.
• 6、 Mimaki, Yoshihiro,Nakamura, Osamu,sashida, Yutaka,Nikaido, Tamotsu,Ohmoto, taichi. "STEROIDAL SAPONINS FROM THE BULBS OF TRITELEIA LACTEA AND THEIR INHIBITORY ACTIVITY ON CYCLIC AMP PHOSPHODIESTERASE". . p. 1279 - 1286. Retrieved 1995.
• 7、 -. "Novel steroid -based amphiphiles and uses thereof". Paragraph 0165; 0170-0171; 0173; 0185-0187; 0239-0241. . Retrieved 2020/05/23.
• 8、 -. "A kind of modified Fischer-type glycosidation reaction in constructing a saponin in the application of the glycosidic bond". Paragraph 0034-0036. . Retrieved 2018/05/24.