1,5,6-Tobmi

Base Information

• Chemical Name: 1,5,6-Tobmi
• CAS No.: 131233-70-0
• Molecular Formula: C27H30 O6
• Molecular Weight: 450.532
• DSSTox Substance ID: DTXSID90927136
• Mol file: 131233-70-0.mol

Synonyms:1,5,6-TOBMI;1,5,6-tri-O-benzyl-myo-inositol;1,5,6-tri-O-benzylmyoinositol

Chemical Property of 1,5,6-Tobmi

Chemical Property:

• Vapor Pressure: 7.55E-15mmHg at 25°C
• Boiling Point: 591.8°Cat760mmHg
• Flash Point: 311.7°C
• PSA: 88.38000
• Density: 1.28g/cm³
• LogP: 2.83890
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 450.20423867
• Heavy Atom Count: 33
• Complexity: 505

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C(C(C(C(C2OCC3=CC=CC=C3)OCC4=CC=CC=C4)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@@H]2[C@@H](C([C@H]([C@@H](C2OCC3=CC=CC=C3)OCC4=CC=CC=C4)O)O)O

Technology Process of 1,5,6-Tobmi

There total 35 articles about 1,5,6-Tobmi 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: 78.0%

(+/-)-1,5,6-tri-O-benzyl-4-O-(prop-1-enyl)-myo-inositol (131146-92-4) → (+/-)-1,5,6-tri-O-benzyl-myo-inositol (131146-93-5,131233-69-7,131233-70-0,145772-95-8)

Guidance literature:

With hydrogenchloride; In methanol; for 0.5h; Heating;

DOI:10.1016/0008-6215(90)80132-M

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → 1D-1,5,6-tri-O-benzyl-myo-inositol (131233-70-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C

2: Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

3: PdCl₂ / dioxane; H₂O / 3 h / 60 °C

4: NaBH₄ / methanol / 0.5 h / 0 °C

5: NaOH / methanol / 12 h / 20 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dichloride; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene; 3: Ferrier-II rearrangement;

DOI:10.1021/jo001575h

Reference yield:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → 1D-1,5,6-tri-O-benzyl-myo-inositol (131233-70-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

2: PdCl₂ / dioxane; H₂O / 3 h / 60 °C

3: NaBH₄ / methanol / 0.5 h / 0 °C

4: NaOH / methanol / 12 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; triethylamine; palladium dichloride; In 1,4-dioxane; methanol; water; 1,2-dichloro-ethane; 2: Ferrier-II rearrangement;

DOI:10.1021/jo001575h

upstream raw materials:

(3aR,4S,5S,6R,7S,7aS)-5,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

D-3-O-acetyl-1,5,6-tri-O-benzyl-myo-inositol

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

1D-1,3,5,6-tetra-O-benzyl-myo-inositol

C₅₄H₆₀O₁₂

C₅₄H₆₀O₁₂

C₅₄H₆₀O₁₂

Refernces

• 1、 Desai, Trupti,Fernandez-Mayoralas, Alfonso,Gigg, Jill,Gigg, Roy,Payne, Sheila. "The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol". . p. 105 - 123. Retrieved 2007/10/02.