3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃

Base Information

• Chemical Name: 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃
• CAS No.: 497067-55-7
• Molecular Formula: C₃₂H₅₁NO₄
• Molecular Weight: 513.761

Synonyms:3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃

Chemical Property of 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃

There total 9 articles about 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D₃ 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:

{(1R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-4-methyl-cyclohex-3-enyl}-carbamic acid tert-butyl ester → 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D3 (497067-55-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo026474t

Reference yield:

(3S,5R)-5-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene (122172-37-6) → 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D3 (497067-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / MeONa / methanol / 2 h / 20 °C

2: 84 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 22 h / 20 °C

3: 100 percent / MeONa / methanol / 2 h / 20 °C

4: 68 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 14 h / 20 °C

5: MeNH₂ / ethanol / 36 h / 20 - 65 °C

6: NaHCO₃ / CHCl₃; H₂O / 24 h / 20 °C

7: Pd(PPh₃)2(OCOCH₃)2; CuI; Et₂NH / dimethylformamide / 1 h / 20 °C

8: Bu₄NF / tetrahydrofuran / 12 h / 20 °C

With copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydrogencarbonate; diethylamine; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jo026474t

Reference yield:

(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene (122172-46-7) → 3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxy-6,7-dehydroprevitamin D3 (497067-55-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 22 h / 20 °C

2: 100 percent / MeONa / methanol / 2 h / 20 °C

3: 68 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 14 h / 20 °C

4: MeNH₂ / ethanol / 36 h / 20 - 65 °C

5: NaHCO₃ / CHCl₃; H₂O / 24 h / 20 °C

6: Pd(PPh₃)2(OCOCH₃)2; CuI; Et₂NH / dimethylformamide / 1 h / 20 °C

7: Bu₄NF / tetrahydrofuran / 12 h / 20 °C

With copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydrogencarbonate; diethylamine; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jo026474t

upstream raw materials:

(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

(3S,5R)-5-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene

(1S,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene

(3S,5S)-3-[(tert-butyldimethylsilyl)oxy]-1-ehtynyl-5-hydroxy-2-methylcyclohex-1-ene

Downstream raw materials:

3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroprevitamin D₃

3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroxyvitamin D₃

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