(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Base Information

Chemical Name:(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
CAS No.:93074-04-5
Deprecated CAS:142407-33-8
Molecular Formula:C₃₂H₄₅NO₇
Molecular Weight:555.712
Hs Code.:
DSSTox Substance ID:DTXSID4058495

(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Synonyms:(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one;93074-04-5;Milbemycin A4 oxime;DTXSID4058495

Suppliers and Price of (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
MilbemycinA4Oxime
2.5mg
$ 2000.00

Cayman Chemical
Milbemycin A4 oxime
5mg
$ 980.00

Cayman Chemical
Milbemycin A4 oxime
1mg
$ 245.00

Total 9 raw suppliers

Chemical Property of (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Chemical Property:

XLogP3:4.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:1
Exact Mass:555.31960277
Heavy Atom Count:40
Complexity:1140

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

MilbemycinA4Oxime ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC1C(CCC2(O1)CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)C
Isomeric SMILES:CC[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]\5[C@@]4([C@@H](C=C(/C5=N/O)C)C(=O)O3)O)C)\C)C
Uses Milbemycin A4 oxime is a semi-synthetic macrocyclic lactone prepared by the oxidation and oximation of a mixture of milbemycin A4. Milbemycin A4 oxime is the major component (~70%) in the commercial product, milbemycin oxime, marketed for endo- and exo-parasite infections. Like the other milbemycin/avermectins, milbemycin A4 oxime acts by opening glutamate sensitive chloride channels in neurons of invertebrates, leading to paralysis by hyperpolarisation of these cells and signal transfer blocking. Milbemycin A4 oxime is the major component of the anti-parasitic product milbemycin oxime.

Technology Process of (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

There total 3 articles about (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21Z,24S)-6'-Ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one 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: 91.4%

: 86691-97-6
5-oxo-5-deoxymilbemycin A₄

: 93074-04-5
5-ketomilbemycin A₄ 5-oxime

Guidance literature:: With hydroxylamine hydrochloride; In 1,4-dioxane; methanol; water; for 6h; Ambient temperature;
DOI:10.1271/bbb1961.55.2615

Reference yield:

: 86691-98-7
5-oxo-5-deoxymilbemycin A₃

: 86691-97-6
5-oxo-5-deoxymilbemycin A₄

: 114177-14-9
5-ketomilbemycin A₃ 5-oxime

: 93074-04-5
5-ketomilbemycin A₄ 5-oxime

Guidance literature:: With hydroxylamine hydrochloride; In 1,4-dioxane; methanol; water; at 5 ℃; Large scale;

Reference yield:

: 51596-11-3
milbemycin A4

: 93074-04-5
5-ketomilbemycin A₄ 5-oxime

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / MnO₂ / acetone / Ambient temperature

2: 91.4 percent / NH₂OH*HCl / H₂O; methanol; dioxane / 6 h / Ambient temperature

With manganese(IV) oxide; hydroxylamine hydrochloride; In 1,4-dioxane; methanol; water; acetone;
DOI:10.1271/bbb1961.55.2615