(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

Base Information

• Chemical Name: (2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane
• CAS No.: 873436-70-5
• Molecular Formula: C₁₉H₃₂O₃Si
• Molecular Weight: 336.547
• Mol file: 873436-70-5.mol

Synonyms:(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

Chemical Property of (2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

There total 1 articles about (2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane 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%

(3R,4S)-3,5-[(S)-benzylidenedioxy]-4-methylpentanol + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane (873436-70-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1002/chem.200500417

Reference yield: 86.0%

(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane (873436-70-5) → (2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol (873436-72-7)

Guidance literature:

With dimethylsulfide borane complex; ZnEt₂*OEt₂; In tetrahydrofuran; hexane; at 50 ℃; for 11.5h;

DOI:10.1002/chem.200500417

Reference yield:

(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane (873436-70-5) → (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide (861701-99-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 86 percent / ZnEt₂*OEt₂; BH₃*SMe₂ / tetrahydrofuran; hexane / 11.5 h / 50 °C

2.1: 90 percent / imidazole; PPh₃; I₂ / benzene / 0.33 h / 20 °C

3.1: iPr₂NEt / acetonitrile / 50 h / Heating

4.1: NaHMDS / toluene / 0.08 h / 20 °C

4.2: toluene / 1 h / 20 °C

5.1: DIBAL / CH₂Cl₂ / 0.33 h / -5 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

7.1: aq. HCl / tetrahydrofuran / 12 h / 20 °C

8.1: DMP / CH₂Cl₂ / 0.5 h / 20 °C

9.1: TEMPO; NaClO₂; NaClO / aq. phosphate buffer; acetonitrile / 2.33 h / 35 °C / pH 7

10.1: aq. CAN / acetonitrile / 0.12 h / 0 °C

11.1: H₂; Et₃N / Pd/C / methanol / 20 h / 20 °C

12.1: 2-methyl-6-nitrobenzoic anhydride; DMAPO; Et₃N / CH₂Cl₂ / 13 h / 20 °C

13.1: TBAF; AcOH / tetrahydrofuran / 13 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; ammonium cerium(IV) nitrate; phthalic acid dimethyl ester; dimethylsulfide borane complex; ZnEt₂*OEt₂; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1002/chem.200500417

upstream raw materials:

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol

(3R,4S,7S,8R)-3-benzyloxy-9-oxo-4,8-dimethylnonan-7-olide

(3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol

(3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide