1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol

Base Information

Chemical Name:1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol
CAS No.:176199-99-8
Molecular Formula:C₁₃H₁₆O₃
Molecular Weight:220.268
Hs Code.:
DSSTox Substance ID:DTXSID901168989

Synonyms:SCHEMBL17265333;DTXSID901168989;1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol;176199-99-8

Suppliers and Price of 1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol

Supply Marketing:

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

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Chemical Property of 1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol

Chemical Property:

XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:220.109944368
Heavy Atom Count:16
Complexity:233

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1C(C(C=CO1)OCC2=CC=CC=C2)O
Isomeric SMILES:C[C@@H]1[C@H]([C@@H](C=CO1)OCC2=CC=CC=C2)O

Technology Process of 1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol

There total 6 articles about 1,5-Anhydro-2,6-dideoxy-3-O-(phenylmethyl)-D-arabino-hex-1-enitol 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%

: 100-39-0
benzyl bromide

: 78086-61-0
(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol

: 176199-99-8
3-O-benzyl-6-deoxy-D-glucal

Guidance literature:: (2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol; With di(n-butyl)tin oxide; In toluene; at 130 ℃; for 4h; Inert atmosphere; Dean-Stark;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; at 130 ℃; for 16h; regioselective reaction; Inert atmosphere; Dean-Stark;
DOI:10.1021/acs.orglett.9b01118

Reference yield:

: 58871-04-8
6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

: 176199-99-8
3-O-benzyl-6-deoxy-D-glucal

Guidance literature:: Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran

2: dibenzyltin oxide; tetra-(n-butyl)ammonium iodide

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; dibenzyltin oxide; In tetrahydrofuran;

Reference yield:

: 2873-29-2
D-glucal triacetate

: 176199-99-8
3-O-benzyl-6-deoxy-D-glucal

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere

2.1: dmap; pyridine / 3 h / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: sodium bromide; sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 65 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 16 h / 80 °C / Inert atmosphere

5.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere

6.1: di(n-butyl)tin oxide / toluene / 4 h / 130 °C / Inert atmosphere; Dean-Stark

6.2: 16 h / 130 °C / Inert atmosphere; Dean-Stark

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; sodium methylate; di(n-butyl)tin oxide; sodium hydrogencarbonate; sodium bromide; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/acs.orglett.9b01118