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-glucopyranose

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-glucopyranose
CAS No.:905714-89-8
Molecular Formula:C₇₀H₇₅NO₂₀
Molecular Weight:1250.36
Hs Code.:

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-glucopyranose

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-glucopyranose

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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-glucopyranose

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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-glucopyranose

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-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: 68.0%

: 905714-88-7
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

: 169106-94-9
2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl fluoride

: 905714-89-8
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-glucopyranose

Guidance literature:: 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; 2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl fluoride; With 4 Angstroem MS; In dichloromethane; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.0833333h;
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

: 905714-89-8
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-glucopyranose

Guidance literature:: Multi-step reaction with 8 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

With pyridine; sodium tetrahydroborate; 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:

: Acetic acid (3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

: 905714-89-8
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-glucopyranose

Guidance literature:: Multi-step reaction with 10 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

With pyridine; sodium tetrahydroborate; 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