(20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 217470-08-1
• Molecular Formula: C₄₁H₇₄O₄Si₂
• Molecular Weight: 687.207
• Mol file: 217470-08-1.mol

Synonyms:

Chemical Property of (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether

There total 18 articles about (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether 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:

5-bromopentanoic acid (2067-33-6) → (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D3 tert-butyldimethylsilyl ether (217470-08-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / acetonitrile / 24 h / 80 °C

2: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

3: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

4: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

5: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

6: 96 percent / DMAP / pyridine / 14 h / 0 °C

7: 92 percent / TBAF / tetrahydrofuran / 20 h / Heating

8: 98 percent / PDC / CH₂Cl₂ / 12 h

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 4 h; -40 deg C, 2 h

10: 94 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

11: 97 percent / DMAP / pyridine / 14 h / -20 °C

12: 1.) CuBr / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, room temperature, 12 h

With tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1021/jo982393e

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D3 tert-butyldimethylsilyl ether (217470-08-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

2: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

4: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

5: 96 percent / DMAP / pyridine / 14 h / 0 °C

6: 92 percent / TBAF / tetrahydrofuran / 20 h / Heating

7: 98 percent / PDC / CH₂Cl₂ / 12 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 4 h; -40 deg C, 2 h

9: 94 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

10: 97 percent / DMAP / pyridine / 14 h / -20 °C

11: 1.) CuBr / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, room temperature, 12 h

With tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo982393e

Reference yield:

(17Z)-8β-<(tert-butyldimethylsilyl)oxy>-des-A,B-21-norcholest-17(20)-en-25-ol (179125-98-5) → (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D3 tert-butyldimethylsilyl ether (217470-08-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

2: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

3: 96 percent / DMAP / pyridine / 14 h / 0 °C

4: 92 percent / TBAF / tetrahydrofuran / 20 h / Heating

5: 98 percent / PDC / CH₂Cl₂ / 12 h

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 4 h; -40 deg C, 2 h

7: 94 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8: 97 percent / DMAP / pyridine / 14 h / -20 °C

9: 1.) CuBr / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, room temperature, 12 h

With tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo982393e

upstream raw materials:

methyllithium

(17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin D₃ tert-butyldimethylsilyl ether

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(20S)-25-<(methoxymethyl)oxy>-des-A,B-cholest-16-en-8-one

Refernces