3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol

Base Information

• Chemical Name: 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol
• CAS No.: 261713-61-5
• Molecular Formula: C₄₆H₆₂O₇Si
• Molecular Weight: 755.08
• Mol file: 261713-61-5.mol

Synonyms:3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol

Chemical Property of 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol

There total 4 articles about 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-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%

tert-butyldimethylsilyl chloride (18162-48-6) + 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol (261713-60-4) → 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol (261713-61-5)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield:

2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane] (261713-59-1) → 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol (261713-61-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂; hexane / 20 °C

2: AlMe₃ / CH₂Cl₂ / 20 °C

3: 91 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 2 h / 20 °C

With dmap; trimethylaluminum; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield:

2,2-Dimethyl-1,3-propanediol (126-30-7) → 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol (261713-61-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / TMSOMe; TMSOTf / toluene / 2 h / 20 °C

2: CH₂Cl₂ / 2 h / 20 °C

3: CH₂Cl₂ / 20 °C

4: 91 percent / Et₃N; DIMAP / dimethylformamide / 3 h / 20 °C

With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Cycloaddition / 2: Ring cleavage / 3: Ring cleavage / 4: Etherification;

DOI:10.1021/ol9913035

upstream raw materials:

tert-butyldimethylsilyl chloride

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol

2,2-Dimethyl-1,3-propanediol

2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane]

Downstream raw materials:

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol

1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-L-xylo-hept-6-en-2-ulose