1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose

Base Information

Chemical Name:1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose
CAS No.:67441-18-3
Molecular Formula:C15H22O6
Molecular Weight:298.336
Hs Code.:
DSSTox Substance ID:DTXSID901155310
Nikkaji Number:J75.593A

Synonyms:DTXSID901155310;1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose;1,2:5,6-Bis-O-(1-methylethylidene)-3-O-2-propyn-1-yl-alpha-D-glucofuranose

Suppliers and Price of 1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

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Total 0 raw suppliers

Chemical Property of 1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose

Chemical Property:

Vapor Pressure:1.83E-05mmHg at 25°C
Boiling Point:374.1°Cat760mmHg
Flash Point:150.4°C
Density:1.21g/cm³
XLogP3:0.6
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:298.14163842
Heavy Atom Count:21
Complexity:450

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC#C)C
Isomeric SMILES:CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)OCC#C)C

Technology Process of 1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose

There total 9 articles about 1-O,2-O:5-O,6-O-Diisopropylidene-3-O-propargyl-alpha-D-glucofuranose 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: 99.0%

: 106-96-7
propargyl bromide

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 67441-18-3
(3aR,4S,5R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4R-yl)-2,2-dimethyl-6-prop-2-ynyloxy-tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

propargyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.3762/bjoc.13.110

Reference yield: 90.0%

: 582-52-5
1,2:5,6-diacetone-D-glucose

: 106-96-7
propargyl bromide

: 67441-18-3,146464-26-8
(3aR,5R,6S,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-prop-2-ynyloxy-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: 1,2:5,6-diacetone-D-glucose; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

propargyl bromide; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 12h;
DOI:10.1002/anie.201502543

Reference yield:

: 142363-22-2
1,2:5,6-di-O-isopropylidene-3-O-(allenyl)-α-D-glucofuranoside

: 67441-18-3
(3aR,4S,5R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4R-yl)-2,2-dimethyl-6-prop-2-ynyloxy-tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / aq. OsO₄; NMO / acetone / 22 h / 20 °C

2: 78 percent / NaH / dimethylformamide / 3 h / 20 °C

3: 81 percent / KOt-Bu / dimethylsulfoxide / 8 h / 140 °C

4: 82 percent / aq. OsO₄; NMO / acetone / 43 h / 20 °C

5: 72 percent / NaH / dimethylformamide / 2.5 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; potassium tert-butylate; sodium hydride; In dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Hydrolysis / 2: Substitution / 3: Isomerization / 4: Hydrolysis / 5: Substitution;
DOI:10.1016/S0040-4020(99)00631-6