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

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Chemical Name:(-)-menthyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside
CAS No.:855271-07-7
Molecular Formula:C₃₀H₄₃NO₁₀
Molecular Weight:577.672
Hs Code.:

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

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

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

There total 15 articles about (-)-menthyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-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: 63.0%

: 855271-05-5
4-pentenyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside

: 2216-51-5
(-)-menthol

: 855271-07-7
(-)-menthyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside

Guidance literature:: 4-pentenyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside; (-)-menthol; With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 23 ℃; for 0.333333h;

With triethylamine; In dichloromethane; at 23 ℃;
DOI:10.1021/jo0500129

Reference yield: 60.0%

: 855271-06-6
4-pentenyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-β-D-mannopyranoside

: 2216-51-5
(-)-menthol

: 855271-07-7
(-)-menthyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside

Guidance literature:: 4-pentenyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-β-D-mannopyranoside; (-)-menthol; With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 23 ℃; for 0.333333h;

With triethylamine; In dichloromethane; at 23 ℃;
DOI:10.1021/jo0500129

Reference yield:

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

: 855271-07-7
(-)-menthyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 8 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: 77 percent / Et₃N; DMAP / tetrahydrofuran / 4 h / 23 °C

4.1: 48 percent / LiOH / tetrahydrofuran; H₂O / 0 - 23 °C

5.1: 96 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 23 °C

6.1: Et₃SiOTf / CH₂Cl₂; H₂O / 23 °C

6.2: 96 percent / Et₃N / CH₂Cl₂ / 23 °C

7.1: 93 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 23 °C

8.1: N-iodosuccinimide; Et₃SiOTf / CH₂Cl₂ / 0.33 h / 23 °C

8.2: 60 percent / Et₃N / CH₂Cl₂ / 23 °C

With pyridine; dmap; lithium hydroxide; N-iodo-succinimide; iodosylbenzene; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; triethylamine; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo0500129