1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose

Base Information

• Chemical Name: 1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose
• CAS No.: 147578-38-9
• Molecular Formula: C₅₁H₅₆O₇Si
• Molecular Weight: 809.087
• Mol file: 147578-38-9.mol

Synonyms:1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose

Chemical Property of 1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose

There total 1 articles about 1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose 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:

(benzyloxymethyl)tributylstannane (66222-28-4) + (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (147556-23-8) → 1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose (147578-38-9)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1) THF, hexane, -80 deg C, 7 min, 2) THF, -80 deg C, 20 min;

DOI:10.1002/recl.19921111205

Reference yield: 81.0%

1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose (147578-38-9) → 2,6-Anhydro-1,3,4,5-tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-D-glycero-D-gulo-heptitol

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h;

DOI:10.1002/recl.19921111205

Reference yield:

1,3,4,5-Tetra-O-benzyl-7-O-(tert-butyldiphenylsilyl)-α-D-glucoheptulopyranose (147578-38-9) → 2,3,4,6-Tetra-O-benzyl-1-O-(3-chlorobenzoyl)β-L-glucopyranose (147568-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / triethylsilane-BF₃*Et₂O / 1,2-dichloro-ethane / 0.5 h / 20 °C

2: 93 percent / tetrabutylammonium fluoride / dioxane / 4 h / 55 °C

3: K₂Cr₂O₇, H₂SO₄ / acetone / 2 h / 55 °C

4: 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.5 h / Ambient temperature

With triethylsilane; potassium dichromate; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; acetone;

DOI:10.1002/recl.19921111205

upstream raw materials:

(benzyloxymethyl)tributylstannane

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

2,6-Anhydro-1,3,4,5-tetra-O-benzyl-D-glycero-D-gulo-heptitol

2,3,4,6-Tetra-O-benzyl-1-O-(3-chlorobenzoyl)β-L-glucopyranose