(1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol

Base Information

• Chemical Name: (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol
• CAS No.: 87649-67-0
• Molecular Formula: C₂₈H₄₄O₂
• Molecular Weight: 412.656
• Mol file: 87649-67-0.mol

Synonyms:(1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol;9,10-Secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1-alpha,3-beta,5Z,7E,22E)-;9,10-Secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1alpha,3beta,5Z,7E,22E)-;Brn 4716774

Chemical Property of (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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• General Description: (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol, also known as (1α,3β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraene-1,3-diol, is a secosteroid derivative structurally related to vitamin D. It features a conjugated triene system and hydroxyl groups at positions 1 and 3, which are critical for its biological activity. (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol is an analog of calcitriol (1,25-dihydroxyvitamin D3) and likely interacts with the vitamin D receptor (VDR), influencing calcium metabolism, cell differentiation, and immune regulation. Its stereochemistry and side-chain modifications may modulate receptor binding affinity and metabolic stability, making it relevant for therapeutic applications in disorders like osteoporosis, psoriasis, or cancer.

Technology Process of (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol

There total 55 articles about (1S,3S,4E)-4-[(2E)-2-[(1R,3aR,7aS)-1-[(E,2S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-6-methylidene-cyclohexane-1,3-diol 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: 99.09%

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (115540-28-8,125136-23-4,111594-58-2,184851-16-9) → doxercalciferol (87649-67-0)

Guidance literature:

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene; With 9-acetylanthracene; In ethyl acetate; at 20 ℃; Inert atmosphere; Irradiation;

With hydrogenchloride; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/op200346g

Reference yield:

→ 1α-Hydroxyergocalciferol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Aus Acetat 11 durch UV-Bestrahlung, Produkt (12) erhitzen, anschl. Rk. mit KOH/Methanol;

DOI:10.1016/0039-128X(77)90056-3

Reference yield:

→ 4-Methylene-5-[2-[7a-methyl-1-((E)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexane-1,3-diol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Acetylverb. (6c) durch Hydrolyse;

DOI:10.1073/pnas.75.5.2080

upstream raw materials:

5,6-cis-1α-Hydroxyvitamin D₂ 3-acetate

3,5-Cyclovitamin D₂

1α-Hydroxy-3,5-cyclovitamin D₂

Vitamin D₂ tosylate

Downstream raw materials:

tert-Butyl-dimethyl-{(S)-5-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-pentyl-cyclohex-3-enyloxy}-silane

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