(1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol

Base Information

• Chemical Name: (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol
• CAS No.: 1346167-12-1
• Molecular Formula: C₂₂H₂₇N₃O₄
• Molecular Weight: 397.474

Synonyms:(1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol

Chemical Property of (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol

Chemical Property:

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Technology Process of (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol

There total 2 articles about (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol 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%

(1R,2R,3R,4R,5R)-4-(acetoxymethyl)-5-azido-1-O-benzoyl-2,3-di-O-benzylcycloheptane (1346167-11-0) → (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol (1346167-12-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1039/c1ob06038d

Reference yield:

(1R,2R,3R,4R,5R)-5-azido-1-benzoyloxy-2,3-dibenzyloxy-4-benzyloxymethyl-cycloheptane (1208102-25-3) → (1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol (1346167-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; zinc(II) chloride / 3 h / 20 °C / Inert atmosphere

2: sodium methylate / methanol / 20 °C / Inert atmosphere

With sodium methylate; acetic acid; zinc(II) chloride; In methanol;

DOI:10.1039/c1ob06038d

Reference yield:

(1R,2R,3R,4R,5R)-5-azido-2,3-di-O-benzyl-4-C-hydroxymethylcycloheptanol (1346167-12-1) → C22H23N3O5 (1346167-13-2)

Guidance literature:

With Jones reagent; In water; acetone; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c1ob06038d

upstream raw materials:

(1R,2R,3R,4R,5R)-5-azido-1-benzoyloxy-2,3-dibenzyloxy-4-benzyloxymethyl-cycloheptane

(1R,2R,3R,4R,5R)-4-(acetoxymethyl)-5-azido-1-O-benzoyl-2,3-di-O-benzylcycloheptane

Downstream raw materials:

C₂₂H₂₃N₃O₅

(1S,2R,3S,7R)-benzyl 7-azido-2,3-di-O-benzyl-4-oxocycloheptanecarboxylate

(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

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