(3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one

Base Information

Chemical Name:(3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one
CAS No.:294209-73-7
Molecular Formula:C₂₈H₂₈O₅
Molecular Weight:444.527
Hs Code.:
DSSTox Substance ID:DTXSID401136759
Nikkaji Number:J1.340.115B

Synonyms:DTXSID401136759;294209-73-7;D-gluco-Hept-6-enonic acid, 6,7-dideoxy-2,3,4-tris-O-(phenylmethyl)-, delta-lactone

Suppliers and Price of (3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one

Supply Marketing:

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

Manufacturers and distributors:

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Chemical Property of (3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one

Chemical Property:

XLogP3:4.8
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:444.19367399
Heavy Atom Count:33
Complexity:589

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C=CC1C(C(C(C(=O)O1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Isomeric SMILES:C=C[C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of (3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one

There total 5 articles about (3R,4S,5R,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-one 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: 85.0%

: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-vinyl-tetrahydro-2H-pyran-2-ol

: 294209-73-7
2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-eno-1,5-lactone

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1002/1521-3773(20000717)39:14<2466::AID-ANIE2466>3.0.CO;2-U

Reference yield:

: 127214-37-3
(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

: 294209-73-7
2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-eno-1,5-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / TfOH / acetic acid / 2.5 h / 80 °C

2: 85 percent / PCC; mol. sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

With trifluorormethanesulfonic acid; 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; acetic acid;
DOI:10.1002/1099-0690(200103)2001:6<1053::aid-ejoc1053>3.3.co;2-j

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,61330-62-9,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2
methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 294209-73-7
2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-eno-1,5-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaOMe / methanol / 2 h

2: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

3: 86 percent / BuLi / tetrahydrofuran / 1.5 h / -78 - 20 °C

4: 75 percent / aq. TfOH / acetic acid / 2.5 h / 80 °C

5: 85 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

With n-butyllithium; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1: Substitution / 2: Oxidation / 3: Condensation / 4: Hydrolysis / 5: Oxidation;
DOI:10.1002/1521-3773(20000717)39:14<2466::AID-ANIE2466>3.0.CO;2-U