S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate

Base Information

• Chemical Name: S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate
• CAS No.: 1335029-85-0
• Molecular Formula: C₃₆H₃₆O₆S₂
• Molecular Weight: 628.81

Synonyms:S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate

Chemical Property of S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate

Chemical Property:

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• Pictogram(s):  
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Technology Process of S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate

There total 5 articles about S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate 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: 70.0%

2,4,6-tri-O-benzyl-1,3-O-benzylidene-5-O-[(methylthio)thiocarbonyl]myo-inositol (1218787-82-6) → 2,4,6-tri-O-benzyl-5-O-[(methylthio)thiocarbonyl]myo-inositol (1218787-88-2) + S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate (1335029-85-0)

Guidance literature:

at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2011.07.044

Reference yield:

6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol (940000-68-0) → S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate (1335029-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil

1.2: 1 h / Reflux

1.3: 16 h / 20 °C

2.1: 12 h / 120 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.1016/j.tet.2011.07.044

Reference yield:

2,4,6-tri-O-benzyl-myo-inositol 1,3,5-orthobenzoate → S-methyl O-((1R,3r,5S,6R,7r,8S,9r)-6,8,9-tris(benzyloxy)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-yl) carbonodithioate (1335029-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil

2.2: 1 h / Reflux

2.3: 16 h / 20 °C

3.1: 12 h / 120 °C / Inert atmosphere

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1016/j.tet.2011.07.044

upstream raw materials:

6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol

2,4,6-tri-O-benzyl-1,3-O-benzylidene-5-O-[(methylthio)thiocarbonyl]myo-inositol

benzyl bromide

Downstream raw materials:

1,3-O-benzylidene-2,4,6-tri-o-benzyl-5-deoxy-myo-inositol

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