(4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

Base Information

• Chemical Name: (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
• CAS No.: 639476-05-4
• Molecular Formula: C₃₁H₄₁NO₆
• Molecular Weight: 523.67

Synonyms:(4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

Chemical Property of (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

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Technology Process of (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

There total 7 articles about (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene 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%

acetic anhydride (108-24-7) + (4R,5S,6R,7R,8R)-N4-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene (639476-04-3) → (4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene (639476-05-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1021/jo034679b

Reference yield:

Benzyl-[(S)-2-benzyloxy-2-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-eth-(E)-ylidene]-amine → (4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene (639476-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / diethyl ether / 0 - 25 °C

2: 88 percent / Et₃N / CH₂Cl₂

With triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/ol0491890

Reference yield:

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0) → (4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene (639476-05-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / Ag₂O / CH₂Cl₂

2: 87 percent / LiAlH₄ / tetrahydrofuran

3: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

4: MgSO₄ / tetrahydrofuran / 2 h / 20 °C

5: 1.31 g / tetrahydrofuran / 2 h / 20 °C

6: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

With dmap; lithium aluminium tetrahydride; magnesium sulfate; Dess-Martin periodane; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034679b

upstream raw materials:

acetic anhydride

(4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

Methyl 3,4:5,6-di-O-isopropylidene-2-O-(benzyl)-D-gluconate

Downstream raw materials:

(2RS,4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidenenonane-1,2-diol

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

(2RS,4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidenenonan-2-ol

(4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidene-2-oxononane

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