1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol

Base Information

• Chemical Name: 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol
• CAS No.: 218462-14-7
• Molecular Formula: C₅₀H₉₄O₃
• Molecular Weight: 747.263

Synonyms:1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol

Chemical Property of 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol

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Technology Process of 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol

There total 12 articles about 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H₂]hexadecyl)-sn-glycerol 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%

isopropylmagnesium bromide (920-39-8) + 1-O-benzyl-2,3-bis-O-((3R,7R,11S)-3,7,11-trimethyl-14-tosyloxy-[14,14-2H2]tetradecyl)-sn-glycerol (218462-06-7) → 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H2]hexadecyl)-sn-glycerol (218462-14-7)

Guidance literature:

With dilithium tetrachlorocuprate; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1246/bcsj.71.2419

Reference yield:

(2S)-3-(benzyloxy)propane-1,2-diol (17325-85-8) → 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H2]hexadecyl)-sn-glycerol (218462-14-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 54 percent / NaH / dimethylsulfoxide / 48 h / Ambient temperature

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

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

4: diethyl ether / 3 h / 0 °C

5: 94 percent / LiAlD₄ / tetrahydrofuran / 12 h / 0 °C

6: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h / 0 °C

7: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 0.17 h / 0 °C

With dmap; sodium tetrahydroborate; jones' reagent; lithium aluminium deuteride; dilithium tetrachlorocuprate; sodium hydride; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1246/bcsj.71.2419

Reference yield:

(R)-3,7-dimethyl-6-octenyl iodide (55816-07-4,59182-95-5,145678-85-9,69308-74-3) → 1-O-benzyl-2,3-di-O-((3R,7R,11S)-3,7,11,15-tetramethyl-[14,14-2H2]hexadecyl)-sn-glycerol (218462-14-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / BuLi, HMPA / tetrahydrofuran; hexane / 4 h / -25 °C

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

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 54 percent / NaH / dimethylsulfoxide / 48 h / Ambient temperature

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

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

7: diethyl ether / 3 h / 0 °C

8: 94 percent / LiAlD₄ / tetrahydrofuran / 12 h / 0 °C

9: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h / 0 °C

10: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 0.17 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; jones' reagent; lithium aluminium deuteride; dilithium tetrachlorocuprate; lithium; sodium hydride; ozone; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ammonia; dimethyl sulfoxide; acetone;

DOI:10.1246/bcsj.71.2419

upstream raw materials:

isopropylmagnesium bromide

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

(2S)-3-(benzyloxy)propane-1,2-diol

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

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