1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol

Base Information

• Chemical Name: 1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol
• CAS No.: 63181-13-5
• Molecular Formula: C27H44O2
• Molecular Weight: 400.64
• UNII: N72HYL8OKC
• DSSTox Substance ID: DTXSID30415284
• Metabolomics Workbench ID: 35784
• Mol file: 63181-13-5.mol

Synonyms:1|A-Calcidol;1beta-Calcidol;N72HYL8OKC;63181-13-5;UNII-N72HYL8OKC;1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol;Alfacalcidol impurity B [EP];(1R,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol;1beta-hydroxyvitamin D3 / 1beta-hydroxycholecalciferol;(5Z,7E)-(1R,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol;(5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1beta,3beta-diol;9,10-Secocholesta-5,7,10(19)-triene-1,3-diol, (1beta,3beta,5Z,7E)-;1.BETA.-CALCIDOL;SCHEMBL9050240;DTXSID30415284;(1R,3R,E)-5-(2-((1R,3aS,7aR,E)-7a-Methyl-1-((R)-6-methylheptan-2-yl)octahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol;1.BETA.-HYDROXY VITAMIN D3;LMST03020235;ALFACALCIDOL IMPURITY B [EP IMPURITY];(1R,3R,5Z,7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1,3-DIOL;9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1,3-DIOL, (1.BETA.,3.BETA.,5Z,7E)-;(1R,3R,Z)-5-(2-((1R,3aS,7aR,E)-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

Chemical Property of 1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol

Chemical Property:

• PSA: 40.46000
• LogP: 6.58980
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 643

Purity/Quality:

98% ^*data from raw suppliers

(1R,3R,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol 98.88% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@H](C3=C)O)O)C
• Uses: An inactive isomeric impurity of Alphacalcidol (A524000).

Technology Process of 1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol

There total 15 articles about 1beta-Hydroxyvitamin D3/1beta-hydroxycholecalciferol 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: 87.0%

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol (86307-24-6,86307-63-3,87649-60-3,87649-61-4,101565-49-5) → 1α-hydroxycholecalciferol (41294-56-8,58028-00-5,63181-13-5,65445-14-9,65445-15-0,76135-93-8,89577-10-6,134523-94-7,142865-40-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00359a061

Reference yield:

1α-hydroxy-3,5-cyclovitamin D3 → 1α-hydroxyvitamin D3 (41294-56-8) + 1α-hydroxy-5,6-trans-vitamin D3 (41294-56-8,58028-00-5,63181-13-5,65445-15-0,76135-93-8,89577-10-6,134523-94-7,142865-40-5,65445-14-9)

Guidance literature:

With acetic acid; In dimethyl sulfoxide; at 50 ℃; for 1h; Overall yield = 87 %; Overall yield = 2.2 g; Inert atmosphere;

DOI:10.1055/s-0033-1339867

Reference yield:

(1S,6R)-3-deoxy-1-hydroxy-6-methoxy-3,5-cyclo-5,6-dihydrovitamin D3 (67657-73-2) → 1α-hydroxyvitamin D3 (41294-56-8) + 1α-hydroxy-5,6-trans-vitamin D3 (41294-56-8,58028-00-5,63181-13-5,65445-15-0,76135-93-8,89577-10-6,134523-94-7,142865-40-5,65445-14-9)

Guidance literature:

With acetic acid; In dimethyl sulfoxide; at 20 - 50 ℃; for 1h; Overall yield = 100 percent; Inert atmosphere;

upstream raw materials:

(1S,6R)-3-deoxy-1-hydroxy-6-methoxy-3,5-cyclo-5,6-dihydrovitamin D₃

vitamin D₃

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol

(S)-3-[(R)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

Downstream raw materials:

1,25-Dihydroxyvitamin D3

1α-hydroxyvitamin D3

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene

Refernces

• 1、 -. "A oral solution of isomer impurities of the directed synthesis method and use thereof (by machine translation)". Paragraph 0028; 0035. . Retrieved 2018/07/30.
• 2、 Ding, Junyuan,Guo, Xianghai,Zeng, Zhouliangzi,Liu, Ningzhi. "A modified synthesis of the antiosteoporosis drug alfacalcidol via a key photochemical transformation of 1α-5,6-Trans-Vitamin D3". . p. 2606 - 2608. Retrieved 2013/12/04.