3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol
• CAS No.: 174810-85-6
• Molecular Formula: C₃₈H₄₆O₃Si₂
• Molecular Weight: 606.952
• Mol file: 174810-85-6.mol

Synonyms:3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property of 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol

There total 9 articles about 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol 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: 91.0%

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol (78086-61-0) + tert-butylchlorodiphenylsilane (58479-61-1) → 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol (174810-85-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; Ambient temperature;

DOI:10.1016/0040-4039(95)02227-9

Reference yield: 85.0%

(2R,3R,4R)-3,4-bis(tert-butyldiphenylsiloxy)-hex-5-yn-2-ol (279684-73-0) → 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol (174810-85-6)

Guidance literature:

With tungsten hexacarbonyl; triethylamine; In tetrahydrofuran; at 50 - 65 ℃; for 5h; UV-irradiation;

DOI:10.1021/ja994229u

Reference yield:

(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one (53723-96-9) → 3,4-bis(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol (174810-85-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / BH₃-SMe₂; (R)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 3.5 h / -45 °C

2: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

3: 94 percent / Ph₃P; DEAD / diethyl ether / 4 h / 20 °C

4: 92 percent / KCN; MeOH / 11 h

5: 91 percent / Ti(O-i-Pr)4 / benzene / 70 °C

6: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

7: 95 percent / DIBAL / CH₂Cl₂ / -70 °C

8: 85 percent / W(CO)6; Et₃N / tetrahydrofuran / 5 h / 50 - 65 °C / UV-irradiation

With 1H-imidazole; titanium(IV) isopropylate; methanol; potassium cyanide; tungsten hexacarbonyl; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dimethylsulfide borane complex; diisobutylaluminium hydride; triethylamine; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Mitsunobu reaction / 4: debenzoylation / 5: Addition / 6: silylation / 7: deacylation / 8: Cyclization;

DOI:10.1021/ja994229u

upstream raw materials:

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol

tert-butylchlorodiphenylsilane

(2R,3R,4R)-3,4-bis(tert-butyldiphenylsiloxy)-hex-5-yn-2-ol

(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one