(2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol

Base Information

• Chemical Name: (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol
• CAS No.: 214533-21-8
• Molecular Formula: C₅₄H₁₀₀O₁₂Si₃
• Molecular Weight: 1025.64
• Mol file: 214533-21-8.mol

Synonyms:(2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol

Chemical Property of (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol

There total 29 articles about (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol 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: 82.0%

(2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-6,12-dimethyl-10-hydroxy-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-11-methoxycarbonyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8; 17,20-diepoxyhenicosane (201336-81-4) → (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol (214533-21-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1248/cpb.46.1199

Reference yield:

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal (186641-79-2) → (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol (214533-21-8)

Guidance literature:

Multi-step reaction with 27 steps

1: CH₂Cl₂ / 10 h / Ambient temperature

2: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

3: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

4: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

5: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

6: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

9: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

10: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

11: 86 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

12: 60 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

13: 90 percent / H₂ / Raney-Ni / ethanol / 760 Torr / Ambient temperature

14: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

15: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 1 h

16: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 2 h

17: Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

18: 86 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

19: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

20: dimethylsulfoxide / 0.5 h / 50 °C

21: K₂CO₃ / methanol / 4 h / Ambient temperature

22: (iso-Pr)2EtN / CH₂Cl₂ / 2 h / Ambient temperature

23: 1.) DIBAH, 2.) aq. Rochelle salt / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, RT, 3 h

24: CrO₃, H₂SO₄ / acetone / 0.5 h / 20 °C

25: diethyl ether

26: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

27: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; benzene;

DOI:10.1248/cpb.46.1199

Reference yield:

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane (186641-76-9) → (2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol (214533-21-8)

Guidance literature:

Multi-step reaction with 28 steps

1: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

2: CH₂Cl₂ / 10 h / Ambient temperature

3: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

4: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

5: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

6: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

7: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

10: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

11: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

12: 86 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

13: 60 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

14: 90 percent / H₂ / Raney-Ni / ethanol / 760 Torr / Ambient temperature

15: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

16: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 1 h

17: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 2 h

18: Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

19: 86 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

20: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

21: dimethylsulfoxide / 0.5 h / 50 °C

22: K₂CO₃ / methanol / 4 h / Ambient temperature

23: (iso-Pr)2EtN / CH₂Cl₂ / 2 h / Ambient temperature

24: 1.) DIBAH, 2.) aq. Rochelle salt / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, RT, 3 h

25: CrO₃, H₂SO₄ / acetone / 0.5 h / 20 °C

26: diethyl ether

27: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

28: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; benzene;

DOI:10.1248/cpb.46.1199

upstream raw materials:

(2R,4S,5S,6R,7R,8S,10S,11R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-6,12-dimethyl-10-hydroxy-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-11-methoxycarbonyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8; 17,20-diepoxyhenicosane

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane

methyl (3R,5R)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

Downstream raw materials:

benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester

(2R,4S,5S,6R,7R,8S,10R,12R,14S,17S,20R)-21-benzoyloxy-1,2-isopropylidenedioxy-6-methyl-11,18-dimethylidene-4,8; 10,14; 17,20-triepoxyhenicosane-5,7-diol

C₅₇H₁₀₆O₁₁Si₄

(2R,4S,5S,6R,7R,8S,10R,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-11,18-dimethylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-10-trimethylsilyloxy-4,8; 17,20-diepoxyhenicosane

Refernces