[(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate

Base Information

• Chemical Name: [(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate
• CAS No.: 13553-79-2
• Molecular Formula: C37H45NO12
• Molecular Weight: 695.764
• Hs Code.: 2941903000
• European Community (EC) Number: 236-938-4
• Mol file: 13553-79-2.mol

Synonyms:13553-79-2

Chemical Property of [(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate

Chemical Property:

• Appearance/Colour: Yellow orange crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 179-181 °C (dec.)
• Refractive Index: 1.605
• Boiling Point: 917.4 °C at 760 mmHg
• PKA: 3.85±0.70(Predicted)
• Flash Point: 508.615 °C
• PSA: 194.99000
• Density: 1.338 g/cm³
• LogP: 3.95910
• Storage Temp.: -20°C Freezer
• Solubility.: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 695.29417587
• Heavy Atom Count: 50
• Complexity: 1480

Purity/Quality:

99%+ ^*data from raw suppliers

Rifamycin S ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=C(C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)C
• Isomeric SMILES: C[C@H]1C=CC=C(C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)[C@](O4)(OC=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)C
• Uses: Semi-synthetic antibiotic. Rifamycin S (Rifaximin EP Impurity E) is a semi-synthetic antibiotic.
• Clinical Use: The rifamycins are a group of chemically related antibioticsobtained by fermentation from cultures of Streptomycesmediterranei. They belong to a class of antibiotics called theansamycins that contain a macrocyclic ring bridged acrosstwo nonadjacent positions of an aromatic nucleus. The termansa means “handle,” describing well the topography of thestructure. The rifamycins and many of their semisynthetic derivativeshave a broad spectrum of antimicrobial activity.They are most notably active against Gram-positive bacteriaand M. tuberculosis. However, they are also active againstsome Gram-negative bacteria and many viruses. Rifampin, asemisynthetic derivative of rifamycin B, was released as anantitubercular agent in the United States in 1971. A secondsemisynthetic derivative, rifabutin, was approved in 1992 forthe treatment of atypical mycobacterial infections.The chemistry of rifamycins and other ansamycins hasbeen reviewed. All of the rifamycins (A, B, C, D, and E) arebiologically active. Some of the semisynthetic derivatives ofrifamycin B are the most potent known inhibitors of DNAdirectedRNA polymerase in bacteria, and their action isbactericidal. They have no activity against the mammalianenzyme. The mechanism of action of rifamycins as inhibitorsof viral replication appears to differ from that for their bactericidalaction. Their net effect is to inhibit the formation of thevirus particle, apparently by preventing a specific polypeptideconversion.77 Rifamycins bind to the β subunit of bacterialDNA-dependent RNA polymerases to prevent chain initiation.78 Bacterial resistance to rifampin has been associatedwith mutations leading to amino acid substitution in the subunit.78 A high level of cross-resistance between variousrifamycins has been observed.

Technology Process of [(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate

There total 20 articles about [(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate 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: 95.0%

rifamycin S-O21,O23 acetonide (51757-14-3) → (+/-)-rifamycin S (13553-79-2,62623-68-1,76188-88-0,81203-58-9,101978-28-3)

Guidance literature:

With perchloric acid; In tetrahydrofuran; water; at 23 ℃; for 4h;

DOI:10.1016/S0040-4039(00)71481-X

Reference yield: 91.0%

rifamycin B (13929-35-6) → rifamycin S (13553-79-2)

Guidance literature:

With hydrogenchloride; In methanol; 1.) 5 min; 2.) room temperature, 5 h;

DOI:10.1246/cl.1982.627

Reference yield: 70.0%

C45H52NO15S(1-)*Na(1+) → rifamycin S (13553-79-2) + 1-[4-(sodiosulfonyl)phenyl]ethan-1-one

Guidance literature:

In ethyl acetate; at 70 ℃; for 4.75h; Product distribution;

DOI:10.1246/bcsj.61.2425

upstream raw materials:

4-[(2R)-2-((S)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-4-deoxy-rifamycin

rifamycin B

rifamycin O

rifamycin S-O₂₁,O₂₃ acetonide

Downstream raw materials:

3-Pyrrolidinomethyl-rifamycin SV

3-<4-Methyl-piperazinomethyl>-rifamycin SV

3-(4-methyl-piperazin-1-yl)-rifamycin

3--rifamycin SV

Refernces

• 1、 Qi, Feifei,Lei, Chao,Li, Fengwei,Zhang, Xingwang,Wang, Jin,Zhang, Wei,Fan, Zhen,Li, Weichao,Tang, Gong-Li,Xiao, Youli,Zhao, Guoping,Li, Shengying. "Deciphering the late steps of rifamycin biosynthesis". . . Retrieved 2018/06/26.
• 2、 L?w, Sebastian A.,Nestl, Bettina M.,Weissenborn, Martin J.,Zepeck, Ferdinand,Hauer, Bernhard. "Process Investigations on the One-Pot Synthesis of Rifamycin S Avoiding Chlorinated Solvents". . p. 1544 - 1547. Retrieved 2015/12/01.