(3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene

Base Information

• Chemical Name: (3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene
• CAS No.: 218461-99-5
• Molecular Formula: C₃₃H₅₀O₃S
• Molecular Weight: 526.824
• Mol file: 218461-99-5.mol

Synonyms:(3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene

Chemical Property of (3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene

There total 1 articles about (3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene 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: 87.0%

(R)-3,7-dimethyl-6-octenyl iodide (55816-07-4,59182-95-5,145678-85-9,69308-74-3) + (2S,6R)-8-(benzyloxy)-1-(phenylsulfonyl)-2,6-dimethyloctane (156592-97-1) → (3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene (218461-99-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -25 ℃; for 4h;

DOI:10.1246/bcsj.71.2419

Reference yield:

(3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene (218461-99-5) → (2S,7R,11R,15S,19S,22S,26S,30R,34R)-2-benzyloxymethyl-7,11,15,19,22,26,30,34-octamethyl-1,4-dioxa-[18,18,23,23-2H4]cyclohexatriacont-20-ene (218462-12-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 64 percent / Li / liquid ammonia; tetrahydrofuran / 1.) -78 deg C, 25 min, 2.) 0 deg C, 2 h

2: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 54 percent / NaH / dimethylsulfoxide / 48 h / Ambient temperature

4: 1.) ozone, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 1.5 h, 2.) MeOH, room temp., 5 h

5: Jones' reagent / acetone / 4 h / 0 °C

6: diethyl ether / 3 h / 0 °C

7: 94 percent / LiAlD₄ / tetrahydrofuran / 12 h / 0 °C

8: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h / 0 °C

9: 91 percent / LiBr / dimethylformamide / 11 h / 50 °C

10: BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.) -78 deg C, 20 min, 2.) room temp., 1 h

11: aq. HCl / tetrahydrofuran; methanol / 12 h / Ambient temperature

12: 48 percent / LiAlH₄ / tetrahydrofuran / 20 h / Ambient temperature

13: 59 percent / tetraisopropyl orthotitanate, D-(-)-diethyl tartrate, t-BuOOH / CH₂Cl₂; decane / 3 h / -25 °C

14: CH₂Cl₂; hexane / 2 h / 0 °C

15: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

16: 60 percent / TiCl₃, Zn-Cu couple / 1,2-dimethoxy-ethane / 62 h / Heating

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; jones' reagent; titanium(III) chloride; lithium aluminium deuteride; diethyl (2S,3S)-tartrate; lithium; copper; sodium hydride; ozone; triethylamine; lithium bromide; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; decane; hexane; dichloromethane; ammonia; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1246/bcsj.71.2419

Reference yield:

(3R,7S,11R)-1-benzyloxy-3,7,11,15-tetramethyl-8-phenylsulfonyl-14-hexadecene (218461-99-5) → (4S,8R,12R)-14-[(S)-2-Benzyloxy-1-((3R,7R,11S)-14-hydroxy-3,7,11-trimethyl-tetradecyloxymethyl)-ethoxy]-4,8,12-trimethyl-tetradecan-1-ol (218462-03-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / Li / liquid ammonia; tetrahydrofuran / 1.) -78 deg C, 25 min, 2.) 0 deg C, 2 h

2: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 54 percent / NaH / dimethylsulfoxide / 48 h / Ambient temperature

4: 1.) ozone, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 1.5 h, 2.) MeOH, room temp., 5 h

With sodium tetrahydroborate; lithium; sodium hydride; ozone; triethylamine; In tetrahydrofuran; dichloromethane; ammonia; dimethyl sulfoxide;

DOI:10.1246/bcsj.71.2419

upstream raw materials:

(R)-3,7-dimethyl-6-octenyl iodide

(2S,6R)-8-(benzyloxy)-1-(phenylsulfonyl)-2,6-dimethyloctane

Downstream raw materials:

(4S,8R,12R)-14-[(S)-2-Benzyloxy-1-((3R,7R,11S)-14-hydroxy-3,7,11-trimethyl-tetradecyloxymethyl)-ethoxy]-4,8,12-trimethyl-tetradecan-1-ol

[(S)-2,3-Bis-((3R,7R,11S)-3,7,11,15-tetramethyl-hexadec-14-enyloxy)-propoxymethyl]-benzene

1-O-benzyl-2,3-bis-O-((3R,7R,11S)-14-hydroxy-3,7,11-trimethyl-[14,14-2H₂]tetradecyl)-sn-glycerol

1-O-benzyl-2,3-bis-O-((3R,7R,11S)-14-bromo-3,7,11-trimethyl-[14,14-2H₂]tetradecyl)-sn-glycerol