214351-86-7

Basic information

• Product Name: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane
• Synonyms: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane
• CAS NO: 214351-86-7
• Molecular Formula: C₁₉H₃₇IOSi
• Molecular Weight: 436.49
• Mol File: 214351-86-7.mol

Chemical Properties

• Boiling Point: 392.6°C at 760 mmHg
• Flash Point: 191.2°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 5.12E-06mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane(214351-86-7)
• EPA Substance Registry System: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane(214351-86-7)

Safety Data

• Hazardous Substances Data: 214351-86-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H37IOSi/c1-14(13-20)15-10-11-16-17(9-8-12-19(15,16)5)21-22(6,7)18(2,3)4/h14-17H,8-13H2,1-7H3

Upstream product

• 171011-48-6 (1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(R)-2-hydroxy-1-methylethyl]-7a-methyl-1H-indene 
• 100928-03-8 (S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol 
• 50-14-6 Calciferol 
• 100928-04-9 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 66774-80-9 (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 
• 104651-47-0 (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 
• 183506-75-4 (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 

Downstream Products

• 182510-45-8 20-epi-25-hydroxyvitamin D₃ 
• 182510-44-7 20-epi-vitamin D₃ 

Relevant articles and documents

Stereoselective Palladium-Catalyzed Approach to Vitamin D3 Derivatives in Protic Medium

We describe an efficient convergent synthesis of vitamin D3 metabolites and analogues. The synthetic strategy relies on a tandem Pd-catalyzed A-ring closure and Suzuki–Miyaura coupling to the CD-side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D3 and 3-epi-vitamin D3 metabolites and analogues modified at the side chain for biological evaluation and structural and metabolic studies.

26- and 27-Methyl groups of 2-substituted, 19-nor-1α,25- dihydroxylated vitamin D compounds are essential for calcium mobilization in vivo

Twelve new analogs of 19-nor-1α,25-dihydroxyvitamin D3 6-17, were prepared by a multi-step procedure from known alcohols 18 and 19. We have examined the influence of removing two methyl groups located at C-25, as well as the 25-hydroxy group, o

Synthesis of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]

A convergent synthesis of biologically interesting 20-epi-eldecalcitol which possesses an inverted C-21 methyl substituent at the 20-position of the side chain of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (eldecalcitol) is described.

Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]

Eldecalcitol [1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3, developing code: ED-71] is an analog of active vitamin D3, 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3] that possesses a hydroxypropoxy substituent at the 2β-position of 1,25(OH)2D3. Eldecalcitol has potent biological effects on bone and is now in preparation for approval as a promising medicine for the treatment of osteoporosis in Japan. To explore chemical structure-biological activity relationships between eldecalcitol and related analogs, we have already synthesized 1-epi-eldecalcitol, 3-epi-eldecalcitol, and 1,3-diepi-eldecalcitol with inherent biological interests of each targeted analog and evaluated their biological responses. It has been reported that 20-epi-1,25(OH)2D3, a diastereomer of 1,25(OH)2D3 that possesses an inverted methyl substituent at the 20-position of the side chain, shows remarkably enhanced biological activities compared to parental compound, 1,25(OH)2D3. As a continuation of our modification studies on eldecalcitol, we took great interest in 20-epi-eldecalcitol and its biological responses. In this paper, the synthesis of 20-epi-eldecalcitol by the Trost coupling reaction between the A-ring fragment and the C/D-ring fragment as well as in vitro preliminary biological evaluation of 20-epi-eldecalcitol are described. In the induction of human myeloid leukemia cell (HL-60) differentiation, inhibition of the human histiocytic lymphoma cell (U937) proliferation, and increase in osteocalcin concentration in the human osteosarcoma cell (MG-63), 20-epi-eldecalcitol showed significantly enhanced activity compared to eldecalcitol.

2alpha-Methyl and 2beta-methyl analogs of 19,26,27-trinor-(20S)-1alpha-hydroxyvitamin D3 and their uses

This invention discloses 2α-methyl and 2β-methyl analogs of 19,26,27-trinor-(20S) -1α-hydroxyvitamin D3 and pharmaceutical uses therefor. These compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells and i

2-METHYLENE-19,26,27-TRINOR-(20S)-1α-ALPHA-HYDROXYVITAMIN D3 AND ITS USES

This invention discloses 2-methylene-19,26,27-trinor-(20S)-vitamin D analogs, and specifically 2-methylene-19,26,27-trinor-(20S)-lα-hydroxyvitamirt D3 and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the

19,26,27-TRINOR-1α,25-DIHYDROXYVITAMIN D3 COMPOUNDS

Compounds of formula (1) are provided where X1, X2, and X3 are independently selected from H or hydroxy protecting groups, and R1 and R2 have the definitions provided herein. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

Vitamin D analogs for obesity prevention and treatment

Methods for treating and preventing obesity, inhibiting adipocyte differentiation, inhibiting increased SCD-1 gene transcription, and/or reducing body fat in a subject include administering at least one analog of 1α,25-dihydroxyvitamin D3 or 1α

Efficient synthesis and biological evaluation of all A-ring diastereomers of 1α,25-dihydroxyvitamin D3 and its 20-epimer

An improved synthesis of the diastereomers of 1α,25-dihydroxyvitamin D3 (1) was accomplished utilizing our practical route to the A-ring synthon. We applied this procedure to synthesize for the first time all possible A- ring diastereomers of 20-epi-1α,25-dihydroxyvitamin D3 (2). Ten-step conversion of 1-(4-methoxyphenoxy)but-3-ene (6), including enantiomeric introduction of the C-3 hydroxyl group to the olefin by the Sharpless asymmetric dihydroxylation, provided all four possible stereoisomers of A- ring enynes (3), i.e., (3R,5R)-, (3R,5S)-, (3S,5R)- and (3S,5S)-bis[(tert- butyldimethylsilyl)oxy]oct-1-en-7-yne, in good overall yield. Palladium- catalyzed cross-coupling of the A-ring synthon with the 20-epi CD-ring portion (5), (E)-(20S)-de-A,B-8-(bromomethylene)cholestan-25-ol, followed by deprotection, afforded the requisite diastereomers of 20-epi-1α,25- dihydroxyvitamin D3 (2). The biological profiles of the synthesized stereoisomers were assessed in terms of affinities for vitamin D receptor (VDR) and vitamin D binding protein (DBP), HL-60 cell differentiation- inducing activity and in vivo calcium-regulating potency in comparison with the natural hormone. (C) 2000 Elsevier Science Ltd.

Synthesis and biological activity of 2-methyl-20-epi analogues of 1α,25-dihydroxyvitamin D3

Synthesis and biological evaluation of all eight possible A-ring diastereomers of 2-methyl-20-epi-1,25-dihydroxyvitamin D3 are described. Among the analogues synthesized, 2α-methyl-20-epi-1α,25-dihydroxyvitamin D3 exhibited exceptionally high potency. The double modification of 2- methyl substitution and 20-epimerization yielded analogues with unique activity profiles.