[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS No.: 107802-83-5
• Molecular Formula: C₆₄H₆₇Cl₃N₂O₂₀
• Molecular Weight: 1290.6
• DSSTox Substance ID: DTXSID901098021
• Nikkaji Number: J1.275.389F

Synonyms:DTXSID901098021;107802-83-5;beta-D-Glucopyranose, O-6-deoxy-2,3,4-tris-O-(phenylmethyl)-alpha-L-galactopyranosyl-(1-->3)-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->4)]-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-6-O-(phenylmethyl)-, 1-(2,2,2-trichloroethanimidate)

Chemical Property of [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate

Chemical Property:

• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 29
• Exact Mass: 1288.335276
• Heavy Atom Count: 89
• Complexity: 2320

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)COCC4=CC=CC=C4)OC(=N)C(Cl)(Cl)Cl)N5C(=O)C6=CC=CC=C6C5=O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)COCC4=CC=CC=C4)OC(=N)C(Cl)(Cl)Cl)N5C(=O)C6=CC=CC=C6C5=O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9

Technology Process of [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate

There total 17 articles about [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate 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: 92.0%

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose (114853-30-4) + trichloroacetonitrile (545-06-2) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (107802-83-5)

Guidance literature:

With sodium hydride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1080/07328300008544072

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (107802-83-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / TsOH / acetonitrile / 0.5 h / 20 °C

2: 97 percent / tetrabutylammonium bromide; diisopropylamine / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

3: 74 percent / sodium cyanoborohydride; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C / pH 1

4: 76 percent / molecular sieves 3 Angstroem; trimethylsilyl triflate / CH₂Cl₂ / 3 h / -70 - -30 °C

5: 92 percent / ammonium and cerium nitrate / acetonitrile; H₂O / 0.08 h / -5 °C

6: 92 percent / NaH / CH₂Cl₂ / 2 h / 0 °C

With ammonium nitrate; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonium and cerium nitrate; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: acetal formation / 2: Substitution / 3: Reduction / 4: glycosylation / 5: Hydrolysis / 6: Addition;

DOI:10.1080/07328300008544072

Reference yield:

benzyl bromide (100-39-0) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (107802-83-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / 1. (Bu₃Sn)2O 2. Bu₄NBr / toluene / 1. 4 h reflux, 2. 16h at 100 deg C

2: 33 percent / BF_3.etherate / 1,2-dichloro-ethane / 4 h / -23 °C / 4 Angstroem molecular sieves

3: 76.8 percent / MeOSO₂CF₃ / diethyl ether / 16 h / 4 Angstroem molecular sieves

4: 65.7 percent / PdCl₂ / aq. acetic acid / 16 h / ultrasonication

5: 67.1 percent / DBU / 1,2-dichloro-ethane / 1 h / 20 °C

With boron trifluoride diethyl etherate; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; methyl trifluoromethanesulfonate; palladium dichloride; In diethyl ether; acetic acid; 1,2-dichloro-ethane; toluene;

DOI:10.1016/0008-6215(87)80279-3

upstream raw materials:

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

trichloroacetonitrile

benzaldehyde dimethyl acetal

p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

1,5-anhydro-6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-arabino-hex-1-enitol

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