3-(Hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol

Base Information

• Chemical Name: 3-(Hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol
• CAS No.: 63167-69-1
• Molecular Formula: C10H18O6
• Molecular Weight: 234.249
• DSSTox Substance ID: DTXSID60408088
• Mol file: 63167-69-1.mol

Synonyms:63167-69-1;3-(hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol;6-(hydroxymethyl)-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol;Methyl 2,3-O-isopropylidene-alpha-D-mannopyranoside;ST51037357;DTXSID60408088;AKOS024386313;Methyl 2,3-O-isopropylidene- alpha -D-mannopyranoside;Methyl 2,3-O-isopropylidene-alpha-D-mannopyranoside, ~98%

Chemical Property of 3-(Hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol

Chemical Property:

• Melting Point: 105 °C
• Boiling Point: 382.9±42.0 °C(Predicted)
• PKA: 12.90±0.70(Predicted)
• PSA: 77.38000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: -0.76900
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 234.11033829
• Heavy Atom Count: 16
• Complexity: 256

Purity/Quality:

95% ^*data from raw suppliers

METHYL-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC(C2O1)OC)CO)O)C

Technology Process of 3-(Hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol

There total 9 articles about 3-(Hydroxymethyl)-5-methoxy-8,8-dimethyl-4,7,9-trioxabicyclo[4.3.0]nonan-2-ol 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: 87.0%

2,2-dimethoxy-propane (77-76-9) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1)

Guidance literature:

With toluene-4-sulfonic acid; In water; at 21 ℃; for 4h;

DOI:10.1039/c7ob00445a

Reference yield: 86.4%

methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside (13035-60-4,50705-56-1,75100-00-4,89387-76-8,118542-52-2,118542-53-3,143996-47-8,143996-48-9) → methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1)

Guidance literature:

With water; acetic acid; at 0 ℃; for 48h;

DOI:10.1016/0008-6215(93)84176-7

Reference yield: 80.0%

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (112612-45-0) → methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside (14133-63-2,14685-82-6,22932-38-3,24562-43-4,33947-10-3,42214-01-7,52572-07-3,72251-91-3,72251-92-4,72959-81-0,104846-19-7,149035-63-2) + methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1)

Guidance literature:

With [Mg₂Cl₃(THF)y]⁺*[AlH_4-nCln]^-; In tetrahydrofuran; at 70 ℃; for 48h;

upstream raw materials:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

acetone

methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

Downstream raw materials:

methyl 2,3-O-isopropylidene-6-O-trityl-α-D-mannopyranoside

methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside

Methyl-4-O-acetyl-2,3-O-isopropyliden-6-O-trityl-α-D-mannopyranosid

methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside