tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose

Base Information

• Chemical Name: tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose
• CAS No.: 124917-60-8
• Molecular Formula: C₃₆H₄₀O₆
• Molecular Weight: 568.71
• Mol file: 124917-60-8.mol

Synonyms:tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose

Chemical Property of tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose

There total 10 articles about tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose 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: 97.0%

ethyl 2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate (116183-75-6) → tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose (124917-60-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

Reference yield:

1-(5α-cholestan-3β-yl)-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)ethanone (124813-83-8,124813-89-4) → Cholestanol (80-97-7) + tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose (124917-60-8)

Guidance literature:

With lithium aluminium tetrahydride; trifluoroacetyl peroxide; Yield given. Multistep reaction. Yields of byproduct given; 1) CH₂Cl₂, 30 min, r.t., 2) diethyl ether, r.t., 2 h;

Reference yield:

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene (82659-52-7) → tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose (124917-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: OsO₄; NaIO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h

2: 1.24 g / NaBH₄ / methanol / 0.5 h

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1021/ol026839w

upstream raw materials:

1-(5α-cholestan-3β-yl)-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)ethanone

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate

Downstream raw materials:

2-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-1-iodoethane

(3S,5S,6R)-3-(2'-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)ethyl)-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde