(1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol

Base Information

• Chemical Name: (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol
• CAS No.: 595566-32-8
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32

Synonyms:(1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol

Chemical Property of (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol

There total 4 articles about (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.0^2,6]dodecane-4,5-diol 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: 80.0%

(2aS,2bR,4R,5R,5aS,7aR)-2-benzyl-2b,4,5,5a-tetrahydro-2-aza-1,6-dioxa-4,5-isopropylidenedioxyfuro[2',3':4,5]bicyclo[4.2.1]nonane (152088-16-9) → (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.02,6]dodecane-4,5-diol (595566-32-8)

Guidance literature:

With sulfuric acid; In water; acetonitrile; at 25 ℃; for 20h;

DOI:10.1016/S0040-4020(03)00634-3

Reference yield:

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.02,6]dodecane-4,5-diol (595566-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / H₂O / 14 h / 25 °C

2: NaIO₄ / CHCl₃; H₂O / 2 h / 25 °C

3: 56 percent / benzene / Heating

4: 80 percent / H₂SO₄ / acetonitrile; H₂O / 20 h / 25 °C

With sodium periodate; sulfuric acid; acetic acid; In chloroform; water; acetonitrile; benzene;

DOI:10.1016/S0040-4020(03)00634-3

Reference yield:

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose (91882-92-7) → (1S,2R,5R,6R,9R)-11-Benzyl-3,7,10-trioxa-11-aza-tricyclo[7.2.1.02,6]dodecane-4,5-diol (595566-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄ / CHCl₃; H₂O / 2 h / 25 °C

2: 56 percent / benzene / Heating

3: 80 percent / H₂SO₄ / acetonitrile; H₂O / 20 h / 25 °C

With sodium periodate; sulfuric acid; In chloroform; water; acetonitrile; benzene;

DOI:10.1016/S0040-4020(03)00634-3

upstream raw materials:

(2aS,2bR,4R,5R,5aS,7aR)-2-benzyl-2b,4,5,5a-tetrahydro-2-aza-1,6-dioxa-4,5-isopropylidenedioxyfuro[2',3':4,5]bicyclo[4.2.1]nonane

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose

Downstream raw materials:

(3S,4R,5R,8R)-4-acetoxy-2-aza-2-benzyl-1,6-dioxa-5-acetoxymethyl-bicyclo[4.2.1]nonane

(1R,4R,5R,6S)-7-Benzyl-4-hydroxymethyl-3,8-dioxa-7-aza-bicyclo[4.2.1]nonan-5-ol

(1S,2R,4R,5R,6S,9R)-5-acetoxy-11-benzyl-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,7,10-trioxa-11-azatricyclo[7.2.1.0^2,6]dodecane

(1R,4S,5R,6S)-7-Benzyl-5-hydroxy-3,8-dioxa-7-aza-bicyclo[4.2.1]nonane-4-carbaldehyde

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