1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol

Base Information

• Chemical Name: 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol
• CAS No.: 252209-28-2
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362

Synonyms:1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol

Chemical Property of 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol

Chemical Property:

Purity/Quality:

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Technology Process of 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol

There total 3 articles about 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol 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:

C18H25NO6 → 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol (252209-28-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; tert-butyl alcohol; for 14h;

DOI:10.1021/ol990904t

Reference yield:

1R(1α,2β,3α,4α,5β)-3-acetoxy-4-benzyloxy-2-(O-benzylhydroxylamino)-1',5-(isopropylidenedioxy)-1-methyl-1-cyclopentanol (252209-26-0) → 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol (252209-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: water / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 20 °C

2: 932 mg / aq. LiOH / tetrahydrofuran; 2-methyl-propan-2-ol / 14 h

With lithium hydroxide; water; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/ol990904t

Reference yield:

2-O-acetyl-3-O-benzyl-1-(O-benzyloximino)-4,6-O-isopropylidene-D-lyxo-hexos-5-ulose → 1R(1α,2β,3α,4α,5β)-2-amino-4-benzyloxy-1',5-(isopropylidenedioxy)-1-methyl-1,3-cyclopentanediol (252209-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / samarium diiodide / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / -30 °C

2: water / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 20 °C

3: 932 mg / aq. LiOH / tetrahydrofuran; 2-methyl-propan-2-ol / 14 h

With lithium hydroxide; samarium diiodide; water; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/ol990904t

upstream raw materials:

1R(1α,2β,3α,4α,5β)-3-acetoxy-4-benzyloxy-2-(O-benzylhydroxylamino)-1',5-(isopropylidenedioxy)-1-methyl-1-cyclopentanol

Downstream raw materials:

C₂₄H₃₀N₂O₆

C₅₁H₅₈N₂SO₁₀

C₂₄H₂₈N₂O₅

C₂₃H₂₆N₂O₅

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