3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol

Base Information

• Chemical Name: 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol
• CAS No.: 282525-31-9
• Molecular Formula: C₂₆H₃₂O₄
• Molecular Weight: 408.538

Synonyms:3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol

Chemical Property of 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol

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Technology Process of 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol

There total 2 articles about 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol 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: 99.0%

benzyl bromide (100-39-0) + 4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol (282525-28-4) → 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol (282525-31-9)

Guidance literature:

4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/jo000110o

Reference yield:

(3aS,6R,6aS)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol (296278-34-7) → 3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol (282525-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 60 percent / tetrahydrofuran / 0.08 h / 0 °C

2.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 0.08 h / 0 °C

2.2: 99 percent / tetrahydrofuran / 24 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1.1: Addition / 2.1: Substitution / 2.2: Alkylation;

DOI:10.1021/jo000110o

Reference yield: 90.0%

3,6-di-O-benzyl-4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol (282525-31-9) → (1R,2R,3S,4R)-1,4-di-O-benzyl-2,3-O-(1-methylethylidene)cyclohept-5-ene-1,2,3,4-tetrol

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo000110o

upstream raw materials:

benzyl bromide

4,5-O-(1-methylethylidene)-1,2,7,8,9-pentadeoxy-D-talo-nona-1,8-dienitol

(3aS,6R,6aS)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

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