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

Base Information

• Chemical Name: (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 228420-90-4
• Molecular Formula: C₄₇H₇₇NO₆Si₂
• Molecular Weight: 808.302
• Mol file: 228420-90-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin 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: 97.0%

phenyl isocyanate (103-71-9) + (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-en-16α-hydroxy-25-<(methoxymethyl)oxy>vitamin D3 tert-butyldimethylsilyl ether (228420-67-5) → (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin D3 tert-butyldimethylsilyl ether (228420-90-4)

Guidance literature:

With dmap; In pyridine; at -20 ℃; for 14h;

DOI:10.1021/jo982393e

Reference yield:

5-bromopentanoic acid (2067-33-6) → (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin D3 tert-butyldimethylsilyl ether (228420-90-4)

Guidance literature:

Multi-step reaction with 11 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

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; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1021/jo982393e

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-ene-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-21-norvitamin D3 tert-butyldimethylsilyl ether (228420-90-4)

Guidance literature:

Multi-step reaction with 10 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

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; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo982393e

upstream raw materials:

phenyl isocyanate

(17E)-1α-<(tert-butyldimethylsilyl)oxy>-17(20)-en-16α-hydroxy-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether

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

(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

Downstream raw materials:

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

(20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>-21-propylvitamin D₃ tert-butyldimethylsilyl ether

Refernces