4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

Base Information

Chemical Name:4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol
CAS No.:443916-44-7
Molecular Formula:C₃₁H₃₃NO₅
Molecular Weight:499.607
Hs Code.:

Synonyms:4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

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Chemical Property of 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

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Technology Process of 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

There total 5 articles about 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol 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: 85.0%

: 108-24-7
acetic anhydride

: (2R,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethynyl-tetrahydro-pyran-3-ylamine

: 443916-44-7
4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1021/jo020054m

Reference yield: 53.0%

: 537031-63-3
(E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene

: 443916-44-7
4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

Guidance literature:: (E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene; With ozone; triphenylphosphine; In dichloromethane;

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃;

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(03)00818-9

Reference yield:

: 180778-36-3
3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

: 443916-44-7
4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOMe; MeOH

2.1: NaH / dimethylformamide / 20 °C

3.1: 87 percent / (Ph₂Me)2IrCOD*PF₆ / tetrahydrofuran / 2 h / 20 °C

4.1: O₃; Ph₃P / CH₂Cl₂

4.2: CBr₄; Ph₃P / CH₂Cl₂ / 20 °C

4.3: 53 percent / LDA / tetrahydrofuran / -78 °C

With methanol; (Ph₂Me)2IrCOD*PF₆; sodium methylate; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)00818-9