Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside

Base Information

• Chemical Name: Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside
• CAS No.: 85716-44-5
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543
• DSSTox Substance ID: DTXSID001152614
• Nikkaji Number: J995.461I
• Mol file: 85716-44-5.mol

Synonyms:DTXSID001152614;Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside;Methyl 6-deoxy-2,3,4-tris-O-(phenylmethyl)-alpha-D-xylo-hex-5-enopyranoside;85716-44-5

Chemical Property of Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 446.20932405
• Heavy Atom Count: 33
• Complexity: 563

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1C(C(C(C(=C)O1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H](C(=C)O1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside

There total 26 articles about Methyl 2-O,3-O,4-O-tribenzyl-5-methylene-alpha-D-xylopyranoside 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%

methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (85716-43-4) → methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside (85716-44-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acschembio.0c00409

Reference yield: 95.0%

methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside (114219-26-0) → methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside (85716-44-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In 1,2-dimethoxyethane; for 3h; Heating;

DOI:10.1055/s-2003-40210

Reference yield: 82.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside (85716-44-5)

Guidance literature:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; With 1H-imidazole; iodine; triphenylphosphine;

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/chem.201501249

upstream raw materials:

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

benzyl bromide

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

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

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

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one

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

Refernces

• 1、 Tardieu, Damien,Desnoyers, Marine,Laye, Claire,Hazelard, Damien,Kern, Nicolas,Compain, Philippe. "Stereoselective Synthesis of C, C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer". supporting information. p. 7262 - 7267. Retrieved 2019/10/11.
• 2、 Ramakrishna, Bandi,Sridhar, Perali Ramu. "Stereoselective synthesis of 1,6-dioxaspirolactones from spiro-cyclopropanecarboxylated sugars: Total synthesis of dihydro-pyrenolide D". supporting information. p. 8142 - 8145. Retrieved 2015/03/04.