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

Base Information

Chemical Name:p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:905714-87-6
Molecular Formula:C₅₀H₆₁NO₁₃Si
Molecular Weight:912.119
Hs Code.:

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

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

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

There total 9 articles about p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 86.0%

: 905714-86-5
p-methoxyphenyl 3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 905714-87-6
p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;
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

: 905714-87-6
p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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

With sodium tetrahydroborate; 4 A molecular sieve; camphor-10-sulfonic acid; 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

: 905714-87-6
p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

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

2: 79 percent / acetic anhydride (Ac₂O); dimethyl sulfoxide (DMSO) / 3 h / 20 °C

3: 75 percent / ethylene glycol; p-toluenesulfonic acid (pTsOH*H₂O) / acetonitrile / 0.5 h / 20 °C

4: 76 percent / NaBH₄ / methanol / 0.02 h / 0 °C

5: 86 percent / Et₃N / dimethylformamide / 0.5 h / 20 °C

With sodium tetrahydroborate; camphor-10-sulfonic acid; acetic anhydride; toluene-4-sulfonic acid; ethylene glycol; dimethyl sulfoxide; triethylamine; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.carres.2006.04.015