2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)-

Base Information

• Chemical Name: 2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)-
• CAS No.: 85798-11-4
• Molecular Formula: C27H26O4
• Molecular Weight: 414.501
• DSSTox Substance ID: DTXSID00473917
• Nikkaji Number: J3.000.656I
• Wikidata: Q82303601
• Mol file: 85798-11-4.mol

Synonyms:85798-11-4;2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)-;DTXSID00473917

Chemical Property of 2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)-

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 414.18310931
• Heavy Atom Count: 31
• Complexity: 556

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C=CC(=O)C(C2OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@H]2C=CC(=O)[C@H]([C@@H]2OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)-

There total 18 articles about 2-Cyclohexen-1-one, 4,5,6-tris(phenylmethoxy)-, (4S,5R,6S)- 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: 91.0%

1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon (85716-45-6) → (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4)

Guidance literature:

With methanesulfonyl chloride; In pyridine;

DOI:10.1016/S0040-4039(00)85830-X

Reference yield: 87.0%

(2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one (606930-14-7) → (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4)

Guidance literature:

With pyridine; dmap; methanesulfonyl chloride; at 20 ℃; for 2h;

DOI:10.1080/07328300701252623

Reference yield: 70.0%

methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside (85716-44-5) → (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4)

Guidance literature:

methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside; With mercury(II) trifluoroacetate; In water; acetone; at 20 ℃; for 8h;

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2011.04.082

upstream raw materials:

1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon

methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside

(2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one

methyl 6-deoxy-α-D-xylo-hex-5-enopyranoside

Downstream raw materials:

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol

1D-(2,4/1,3)-1,2,3-tri-O-benzyl-4-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol

C₂₁H₂₀O₄

(4S,5R,6S)-4,5,6-tris(benzyloxy)-2-methylcyclohex-2-enone

Refernces

• 1、 Lastdrager, Bas,Timmer, Mattie S. M.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Overhand, Mark. "Transformation of glucose into a novel carbasugar amino acid dipeptide isostere". . p. 41 - 59. Retrieved 2008/04/18.
• 2、 Takahashi, Hideyo,Iimori, Takamasa,Ikegami, Shiro. "An efficient synthesis of cyclophellitol utilizing unusual regioselectivity of oxirane ring opening with Mes2BCH2Li". . p. 6939 - 6942. Retrieved 2007/10/03.