1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose

Base Information

• Chemical Name: 1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose
• CAS No.: 42926-89-6
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• European Community (EC) Number: 610-086-7
• DSSTox Substance ID: DTXSID001181445
• Nikkaji Number: J2.333.217E

Synonyms:SCHEMBL19889852;DTXSID001181445;1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose;(5S)-1-O,2-O-Isopropylidene-3-O-benzyl-5-(hydroxymethyl)-alpha-D-xylofuranose;42926-89-6

Chemical Property of 1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 310.14163842
• Heavy Atom Count: 22
• Complexity: 368

Purity/Quality:

purity more 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(CO)O)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@H](CO)O)OCC3=CC=CC=C3)C

Technology Process of 1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose

There total 25 articles about 1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-beta-L-idofuranose 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: 93.0%

C19H26O6 → 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (22529-61-9,34370-88-2,40982-91-0,42926-89-6,57099-04-4,65434-49-3,134275-39-1)

Guidance literature:

With phosphotungstic acid; water; In acetonitrile; at 20 ℃; for 5h; chemoselective reaction;

DOI:10.1016/j.tetlet.2011.05.050

Reference yield: 83.0%

3-O-benzyl-1,2-O-isopropylidene-6-O-tetrahydropyranyl-β-L-idofuranose → 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose (42926-89-6)

Guidance literature:

With methanol; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2009.11.084

Reference yield: 78.0%

1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(dimethyl-phenyl-silanyl)-ethanol → (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose (42926-89-6)

Guidance literature:

With peracetic acid; sodium acetate; sodium bromide; In acetic acid; at 0 ℃; for 2h;

DOI:10.1002/recl.19931120704

upstream raw materials:

5.6-Di-O-benzoyl-3-O-benzyl-1.2-O-isopropyliden-β-L-idofuranose

3-O-benzyl-6-C-<(E)-6-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropyledene-α-D-glucofuranose

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

3-O-benzyl-L-idopyranose

(2R,3S,4R,5S)-3-Benzyloxy-2,4,6-trihydroxy-5-methoxy-hexanal

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