2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside
• CAS No.: 125034-38-0
• Molecular Formula: C₅₉H₁₁₃NO₁₁Si₃
• Molecular Weight: 1096.8
• Mol file: 125034-38-0.mol

Synonyms:2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

Chemical Property of 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

There total 1 articles about 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-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: 97.0%

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside (125056-32-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside (125034-38-0)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/0008-6215(90)84152-K

Reference yield: 88.0%

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside (125034-38-0) + chlorophosphoric acid diphenyl ester (2524-64-3) → 2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside (125056-33-9)

Guidance literature:

With dmap; In pyridine; dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(90)84152-K

Reference yield:

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside (125034-38-0) → (R)-3-Undecanoyloxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-6-hydroxy-2-hydroxymethyl-5-((R)-3-hydroxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / 4-(dimethylamino)pyridine (DMAP) / pyridine; CH₂Cl₂ / Ambient temperature

2: 86.6 percent / H₂ / 10percent palladium-on-carbon / methanol

3: 4-(dimethylamino)pyridine (DMAP), 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide hydrochloride (WSC) / CH₂Cl₂ / Ambient temperature

4: boron trifluoride etherate / CH₂Cl₂ / 0 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/0008-6215(90)84152-K

upstream raw materials:

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-hydroxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 3-O-<(3R)-3-acetoxytetradecanoyl>-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-octanoyloxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside