(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Base Information

Chemical Name:(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside
CAS No.:855270-93-8
Molecular Formula:C₂₉H₄₃NO₈
Molecular Weight:533.662
Hs Code.:

Synonyms:(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

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Chemical Property of (-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

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Technology Process of (-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

There total 8 articles about (-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside 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: 97.0%

: 855270-91-6
(-)-menthyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

: 108-24-7
acetic anhydride

: 855270-93-8
(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Guidance literature:: With pyridine; dmap; In dichloromethane;
DOI:10.1021/jo0500129

Reference yield:

: 855270-65-4
3-O-carbamoyl-4,6-O-isopropylidene-D-glucal

: 855270-93-8
(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: iodosobenzene; molecular sieves 4 Angstroem / Rh₂(OAc)4 / CH₂Cl₂ / 25 h / 23 °C

2: 92 percent / Et₃N; DMAP / tetrahydrofuran / 4 h / 23 °C

3: 71 percent / iodonium di-sym-collidine perchlorate; molecular sieves 4 Angstroem / CH₂Cl₂ / 17 h / 23 °C

4: 47 percent / sodium hydride / methanol; toluene / 0.75 h / -70 - -15 °C

5: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; iodonium(di-γ-collidine) perchlorate; iodosylbenzene; 4 A molecular sieve; sodium hydride; triethylamine; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo0500129

Reference yield:

: 51450-36-3
4,6-O-isopropylidene-D-glucal

: 855270-93-8
(-)-menthyl 3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 0 - 23 °C

1.2: 71 percent / K₂CO₃ / methanol; CH₂Cl₂ / 0 - 23 °C

2.1: iodosobenzene; molecular sieves 4 Angstroem / Rh₂(OAc)4 / CH₂Cl₂ / 25 h / 23 °C

3.1: 92 percent / Et₃N; DMAP / tetrahydrofuran / 4 h / 23 °C

4.1: 71 percent / iodonium di-sym-collidine perchlorate; molecular sieves 4 Angstroem / CH₂Cl₂ / 17 h / 23 °C

5.1: 47 percent / sodium hydride / methanol; toluene / 0.75 h / -70 - -15 °C

6.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; iodonium(di-γ-collidine) perchlorate; iodosylbenzene; 4 A molecular sieve; sodium hydride; triethylamine; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo0500129