allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

Base Information

• Chemical Name: allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside
• CAS No.: 821794-31-4
• Molecular Formula: C₅₁H₅₉NO₁₈Si
• Molecular Weight: 1002.11
• Mol file: 821794-31-4.mol

Synonyms:allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

Chemical Property of allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

There total 11 articles about allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside 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: 98.0%

allyl 2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside (821794-30-3) + Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-4-allyloxycarbonyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (821794-18-7) → allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside (821794-31-4)

Guidance literature:

With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200400255

Reference yield:

aldehydo-L-Galactose (15572-79-9) → allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside (821794-31-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 30 percent / acetyl chloride / 70 °C

2: 97 percent / pyridine; Et₃N / CH₂Cl₂ / 20 °C

3: p-toluenesulfonic acid / dimethylformamide / 3 h / pH 3

4: 0.33 mg / pyridine / 20 °C

5: trifluoroacetic acid; H₂O / CH₂Cl₂ / 3 h

6: p-toluenesulfonic acid / CH₂Cl₂ / 20 °C / pH 3

7: 0.15 g / aq. acetic acid / 0.25 h / 40 °C

8: 98 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 4 A molecular sieve; water; toluene-4-sulfonic acid; acetic acid; triethylamine; acetyl chloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200400255

Reference yield:

4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-36-2) → allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside (821794-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C

2: 1.3 g / pyridine / 20 °C

3: ammonium cerium(IV) nitrate / toluene; acetonitrile; H₂O / 1 h / 20 °C

4: 0.6 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h / 0 °C

5: 98 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

With pyridine; ammonium cerium(IV) nitrate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/ejoc.200400255

upstream raw materials:

allyl 2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-4-allyloxycarbonyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

aldehydo-L-Galactose

4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside