benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Base Information

Chemical Name:benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside
CAS No.:484647-54-3
Molecular Formula:C₇₂H₈₅NO₁₄Si
Molecular Weight:1216.55
Hs Code.:

benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Synonyms:benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

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Chemical Property of benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

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Technology Process of benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

There total 14 articles about benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside 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: 88.0%

: 484647-42-9
2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate

: 484647-53-2
benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

: 484647-54-3
benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ja028386w

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-Mannose pentaacetate

: 484647-54-3
benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: HBr; AcOH / CH₂Cl₂ / 2 h / 20 °C

2.1: 2,6-lutidine; 3 Angstroem molecular sieves / 18 h / 20 °C

3.1: K₂CO₃ / methanol / 6 h / 20 °C

4.1: imidazole / dimethylformamide / 5 h / 20 °C

5.1: 412.1 mg / tetrabutylammonium iodide; NaH / dimethylformamide / 16 h / 20 °C

6.1: Dowex resin / aq. ethanol / 6 h / 20 °C

6.2: 60 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

7.1: 88 percent / TMSOTf / CH₂Cl₂; diethyl ether / 2 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; Dowex resin; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; hydrogen bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja028386w

Reference yield:

: 3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0
3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

: 484647-54-3
benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: K₂CO₃ / methanol / 6 h / 20 °C

2.1: imidazole / dimethylformamide / 5 h / 20 °C

3.1: 412.1 mg / tetrabutylammonium iodide; NaH / dimethylformamide / 16 h / 20 °C

4.1: Dowex resin / aq. ethanol / 6 h / 20 °C

4.2: 60 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

5.1: 88 percent / TMSOTf / CH₂Cl₂; diethyl ether / 2 h / 20 °C

With 1H-imidazole; Dowex resin; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja028386w