OSW-1

Base Information

• Chemical Name: OSW-1
• CAS No.: 145075-81-6
• Molecular Formula: C47H68 O15
• Molecular Weight: 873.048
• Mol file: 145075-81-6.mol

Synonyms:OSW1; Orsaponin

Chemical Property of OSW-1

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 932.5 °C at 760 mmHg
• PKA: 12.65±0.70(Predicted)
• Flash Point: 267 °C
• PSA: 216.97000
• Density: 1.31 g/cm³
• LogP: 4.02410
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

OSW-1,>90%(Orsaponin) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: OSW-1 is a saponin that has been found in O. saundersiae and has antiviral and anticancer activities. It is an inhibitor of oxysterol-binding protein (OSBP) and its paralog OSBP-related protein 4 (ORP4) with Ki values of 16 and 71 nM, respectively, in radioligand binding assays using HEK293T cell lysates. It induces OSBP translocalization from the cytoplasm to the trans-Golgi network and decreases intracellular levels of OSBP in HEK293 cells. OSW-1 inhibits replication of a variety of enteroviruses (IC50s = 2.4-9.4 nM), including replication of coxsackievirus B3 (CVB3) in infected HeLa R19 cells in an OSBP-dependent manner when used at a concentration of 3 nM. It also inhibits replication of hepatitis C virus (HCV) but not mouse hepatitis virus (MHV), a coronavirus. It protects against CVA9 and echovirus 2 infection in HeLa cells when used at a concentration of 10 nM. OSW-1 inhibits growth of HeLa and HEK293 cells (GI50s = 0.33 and 0.22 nM, respectively).
• Uses: OSW-1 is a unique steroidal saponin displaying selective cytotoxicity against cancer cell lines. From Ornithogalum Saundersiae bulbs.

Technology Process of OSW-1

There total 76 articles about OSW-1 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: 82.0%

C71H124O15Si4 → 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside} (145075-81-6)

Guidance literature:

With water; dichloro bis(acetonitrile) palladium(II); In acetone; at 20 ℃;

DOI:10.1021/jo051536b

Reference yield: 81.0%

C77H116O18Si2 (335197-29-0) → 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside} (145075-81-6)

Guidance literature:

C₇₇H₁₁₆O₁₈Si₂; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 25 ℃; for 12h;

With bis(acetonitrile)palladium(II) dichloride; In water; acetone; at 25 ℃; for 2h; Further stages.;

DOI:10.1021/ja004098t

Reference yield: 79.0%

(20S,23Z,25Z)-3β,16β,17α-trihydroxy-23,26-epithio-3β-cholesta-5,23,25-trien-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-α-L-arabinopyranoside} → 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside} (145075-81-6)

Guidance literature:

With hydrogen; nickel; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2007.11.087

upstream raw materials:

C₇₃H₁₂₈O₁₆Si₄

C₇₇H₁₁₆O₁₈Si₂

C₆₆H₁₁₂O₁₅Si₃

C₇₁H₁₂₆O₁₅Si₄

Downstream raw materials:

4-methoxybenzoic acid

3β,17α-dihydroxy-16β-[(O-β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one

C₅₈H₈₀N₄O₁₉S

Refernces

• 1、 Shi, Bingfeng,Tang, Pingping,Hu, Xiaoyi,Liu, Jun O.,Yu, Biao. "OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities". . p. 10354 - 10367. Retrieved 2007/10/03.
• 2、 Yu, Wensheng,Jin, Zhendong. "Total synthesis of the anticancer natural product OSW-1". . p. 6576 - 6583. Retrieved 2007/10/03.