2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 117253-05-1
• Molecular Formula: C₃₂H₄₂O₆Si
• Molecular Weight: 550.767
• Mol file: 117253-05-1.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 10 articles about 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 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: 79.0%

2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (117253-04-0) → 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (117253-05-1)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; at 22 ℃;

DOI:10.1021/jo00259a006

Reference yield: 51.0%

2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (189744-16-9) → 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (117253-05-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1002/chem.201203865

Reference yield:

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (81342-44-1) → 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (117253-05-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / CH₃ONa / methanol / 3 h

2: 83 percent / p-TsOH*H₂O / tetrahydrofuran / 27 h / 22 °C

3: 4 percent / t-Bu₄NHSO₄, 1.3 M aq. NaOH / CH₂Cl₂ / 48 h / Heating

4: 79 percent / ethereal HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 22 °C

With hydrogenchloride; sodium hydroxide; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; tetra-tert-butylammonium hydrogen sulfate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00259a006

upstream raw materials:

2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

N-(selenocarbamido)piperidine

2-(Trimethylsilyl)ethanol

benzaldehyde dimethyl acetal

Downstream raw materials:

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(6-O-benzoyl-2-deoxy-2-iodo-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside