2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

Base Information

• Chemical Name: 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• CAS No.: 905714-90-1
• Molecular Formula: C₇₀H₇₄FNO₁₉
• Molecular Weight: 1252.35

Synonyms:2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

Chemical Property of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

There total 12 articles about 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 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:

Acetic acid (3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (905714-90-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 4 Angstroem molecularsieves / CH₂Cl₂ / 1 h

1.2: trimethylsilyl triflate (TMSOTf) / CH₂Cl₂ / 0.08 h / 0 °C

2.1: NaOMe / methanol; CH₂Cl₂ / 20 °C

3.1: 0.10 g / D-camphor-10-sulfonic acid monohydrate / acetonitrile / 1 h

4.1: 79 percent / acetic anhydride (Ac₂O); dimethyl sulfoxide (DMSO) / 3 h / 20 °C

5.1: 75 percent / ethylene glycol; p-toluenesulfonic acid (pTsOH*H₂O) / acetonitrile / 0.5 h / 20 °C

6.1: 76 percent / NaBH₄ / methanol / 0.02 h / 0 °C

7.1: 86 percent / Et₃N / dimethylformamide / 0.5 h / 20 °C

8.1: Et₃N / 0.5 h / 20 °C

9.1: 18 mg / HF; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 4 Angstroem MS / CH₂Cl₂ / 1 h

10.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / 0 °C

11.1: 77 percent / dimethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; sodium tetrahydroborate; dimethylaminosulphur trifluoride; 4 A molecular sieve; 4 Angstroem MS; camphor-10-sulfonic acid; hydrogen fluoride; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; ethylene glycol; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2006.04.015

Reference yield:

2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (905714-90-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 0.10 g / D-camphor-10-sulfonic acid monohydrate / acetonitrile / 1 h

2.1: 79 percent / acetic anhydride (Ac₂O); dimethyl sulfoxide (DMSO) / 3 h / 20 °C

3.1: 75 percent / ethylene glycol; p-toluenesulfonic acid (pTsOH*H₂O) / acetonitrile / 0.5 h / 20 °C

4.1: 76 percent / NaBH₄ / methanol / 0.02 h / 0 °C

5.1: 86 percent / Et₃N / dimethylformamide / 0.5 h / 20 °C

6.1: Et₃N / 0.5 h / 20 °C

7.1: 18 mg / HF; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 4 Angstroem MS / CH₂Cl₂ / 1 h

8.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / 0 °C

9.1: 77 percent / dimethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; sodium tetrahydroborate; dimethylaminosulphur trifluoride; 4 Angstroem MS; camphor-10-sulfonic acid; hydrogen fluoride; acetic anhydride; toluene-4-sulfonic acid; ethylene glycol; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2006.04.015

Reference yield:

p-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-arabino-hex-2-ulopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (905714-83-2) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (905714-90-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 75 percent / ethylene glycol; p-toluenesulfonic acid (pTsOH*H₂O) / acetonitrile / 0.5 h / 20 °C

2.1: 76 percent / NaBH₄ / methanol / 0.02 h / 0 °C

3.1: 86 percent / Et₃N / dimethylformamide / 0.5 h / 20 °C

4.1: Et₃N / 0.5 h / 20 °C

5.1: 18 mg / HF; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 4 Angstroem MS / CH₂Cl₂ / 1 h

6.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / 0 °C

7.1: 77 percent / dimethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; sodium tetrahydroborate; dimethylaminosulphur trifluoride; 4 Angstroem MS; hydrogen fluoride; toluene-4-sulfonic acid; ethylene glycol; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2006.04.015

upstream raw materials:

p-methoxyphenyl 3-O-allyl-β-D-arabino-hex-2-ulopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-methoxyphenyl 3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-arabino-hex-2-ulopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-methoxyphenyl 2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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