vitamin D₃ 3,5-dinitrobenzoate

Base Information

• Chemical Name: vitamin D₃ 3,5-dinitrobenzoate
• CAS No.: 1183-41-1
• Molecular Formula: C₃₄H₄₆N₂O₆
• Molecular Weight: 578.749
• Mol file: 1183-41-1.mol

Synonyms:

Chemical Property of vitamin D₃ 3,5-dinitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of vitamin D₃ 3,5-dinitrobenzoate

There total 29 articles about vitamin D₃ 3,5-dinitrobenzoate 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: 80.0%

vitamin D3 (67-97-0) + 3,5-dinitrobenoyl chloride (99-33-2) → vitamin D3 3,5-dinitrobenzoate (1183-41-1,60413-82-3)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00376a049

Reference yield:

(-)-<1(S)-methyl-2(S)-((phenylsylfonyl)methyl)-5(R)-(1(R),5-dimethylhexyl)cyclopentyl>acetaldehyde (96685-46-0) → vitamin D3 3,5-dinitrobenzoate (1183-41-1,60413-82-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, 0 deg C, 30 min

2: 50 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

3: pyridine / 1 h / 0 °C

4: 1.) LiBr, Li₂CO₃, DMF, 2.) H₂ / 2.) 5percent Pd/C / 1.) 150 deg C, 4 h, 2.) ethyl acetate, RT, 8 h

6: 5percent sodium amalgam / tetrahydrofuran; methanol / 9 h / -20 - 20 °C

7: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

8: 80 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; lithium carbonate; triethylamine; N,N-dimethyl-formamide; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00376a049

Reference yield:

(-)-(1S,3aR,4R,7aS)-1-<(phenylsulfonyl)methyl>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan-5-one (96843-38-8) → vitamin D3 3,5-dinitrobenzoate (1183-41-1,60413-82-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / p-toluenesulfonic acid / 10 h / Heating

2: 1.) O₃, 2.) LiOH / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) THF, RT, 2 h

3: 73 percent / camphorsulfonic acid / benzene / 2 h / Heating

4: 72 percent / LiAlH₄ / tetrahydrofuran / 9 h / Ambient temperature

5: 93 percent / 4-(dimethylamino)pyridine, pyridine / 5 h / Ambient temperature

6: 95 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

7: 95 percent / HCl / acetone / 6 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, 0 deg C, 30 min

9: 50 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

10: pyridine / 1 h / 0 °C

11: 1.) LiBr, Li₂CO₃, DMF, 2.) H₂ / 2.) 5percent Pd/C / 1.) 150 deg C, 4 h, 2.) ethyl acetate, RT, 8 h

13: 5percent sodium amalgam / tetrahydrofuran; methanol / 9 h / -20 - 20 °C

14: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

15: 80 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; lithium hydroxide; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; lithium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; N,N-dimethyl-formamide; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; benzene;

DOI:10.1021/jo00376a049

upstream raw materials:

previtamin D₃

benzene

(3S)-3-(3,5-dinitro-benzoyloxy)-9,10-seco-cholesta-5⁽¹⁰⁾,6c,8-triene

vitamin D₃

Downstream raw materials:

(3S)-3-(3,5-dinitro-benzoyloxy)-9,10-seco-cholesta-5⁽¹⁰⁾,6c,8-triene

9,10-seco-cholestadiene-(7,10⁽¹⁹⁾)-triol-(3,5,6)

Refernces

• 1、 Yakhimovich, R. I.,Esaulenko, A. N.,Yusupova, L. M.,Turov, A. V.,Bauman, V. K.,Valinietse, M. Yu.. "SYNTHESIS OF VITAMIN D3 ESTERS". . p. 661 - 664. Retrieved 2007/10/02.
• 2、 Kocienski, Philip J.,Lythgoe, Basil. "Calciferol and its Relatives. Part 27. A Synthesis of 1α-Hydroxyvitamin D3 by way of 1α-Hydroxytachysterol3". . p. 1400 - 1404. Retrieved 2007/10/02.