Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside

Base Information

• Chemical Name: Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside
• CAS No.: 4594-60-9
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.223
• DSSTox Substance ID: DTXSID00473119
• Nikkaji Number: J1.132.161E
• Mol file: 4594-60-9.mol

Synonyms:4594-60-9;Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside;(3aR,6R,7S,7aS)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol;SCHEMBL7144978;DTXSID00473119;METHYL-3,4-O-ISOPROPYLIDENE-BETA-D-ARABINOPYRANOSIDE;W-202812;Methyl 3,4-O-(1-methylethylidene)-beta-D-arabinopyranoside

Chemical Property of Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside

Chemical Property:

• PSA: 57.15000
• LogP: -0.12990
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 204.09977361
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

95% ^*data from raw suppliers

Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2COC(C(C2O1)O)OC)C
• Isomeric SMILES: CC1(O[C@@H]2CO[C@H]([C@H]([C@@H]2O1)O)OC)C

Technology Process of Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside

There total 17 articles about Methyl 3,4-O-isopropylidene-b-D-arabinopyranoside 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: 89.0%

2,2-dimethoxy-propane (77-76-9) + methyl-β-D-arabinopyranoside (5328-63-2) → methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (4594-60-9,817620-70-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;

DOI:10.1016/j.tet.2004.04.040

Reference yield:

methyl-β-D-arabinopyranoside (5328-63-2) → methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (4594-60-9,817620-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / deuterium oxide / deuterated Raney nickel / 15 h / Heating

2: Ts-OH / dimethylformamide

With water-d2; toluene-4-sulfonic acid; deuterated Raney nickel; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)83465-7

Reference yield:

→ O2,O2'-methanediyl-bis-[methyl-(O3,O4-isopropyliden-β-D-arabinopyranoside] (115048-19-6) + methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (4594-60-9,817620-70-5)

Guidance literature:

With ethanol; nickel; benzene;

DOI:10.1021/ja01592a043

upstream raw materials:

acetone

methyl-β-D-arabinopyranoside

methanol

2,2-dimethoxy-propane

Downstream raw materials:

methyl 3,4-O-isopropylidene-2-O-methanesulfonyl-β-D-arabinopyranoside

methyl-3,4-O-isopropylidene-2-O-tosyl-β-D-arabinopyranoside

O¹,O²;O³,O⁴-diisopropylidene-β-D-arabinopyranose

methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside