benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

Base Information

• Chemical Name: benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside
• CAS No.: 86964-41-2
• Molecular Formula: C₂₈H₃₄F₃NO₇
• Molecular Weight: 553.576
• Mol file: 86964-41-2.mol

Synonyms:benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

Chemical Property of benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

There total 7 articles about benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside 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: 76.0%

benzyl 4-O-(4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (86964-40-1) → benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (86964-41-2)

Guidance literature:

With sodium hydroxide; In methanol; for 18h;

DOI:10.1016/0008-6215(90)80090-P

Reference yield:

benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (81703-97-1) → benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (86964-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) bromotrimethylsilane, 2.) HgBr₂, HgO / 1.) benzene, r.t., 2.) CH₂Cl₂, 15 min 0 deg C then 1 h r.t.

2: NaOMe / methanol

With trimethylsilyl bromide; sodium methylate; mercury dibromide; mercury(II) oxide; In methanol;

DOI:10.1039/c39830000305

Reference yield:

4-O-acetyl-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol (106988-71-0,131896-91-8) → benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (86964-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / trimsyl triflate, powdered molecular sieves (4 Angstroem), triethylamine / CH₂Cl₂ / -60 °C

2: 76 percent / 0.5M aq. NaOH / methanol / 18 h

With sodium hydroxide; 4 A molecular sieve; trimsyl triflate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/0008-6215(90)80090-P

upstream raw materials:

benzyl 4-O-(4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

methyl-3-O-benzyl-2,6-didesoxy-β-L-lyxo-hexopyranoside

Downstream raw materials:

benzyl 4)-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-(1->4)-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside)>

Acetic acid (2S,3R,4R,5R,6S)-3-acetoxy-6-{(2S,3R,4S,6S)-4-benzyloxy-6-[(2S,3S,4S,6R)-6-benzyloxy-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-5-iodo-2-methyl-tetrahydro-pyran-4-yl ester

(2S,3S,4S,6S)-6-[(2S,3R,4S,6S)-6-((2S,3S,4S,6R)-4-Amino-6-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3,4-diol

(2S,3R,4S,6S)-6-((2S,3S,4S,6R)-4-Amino-6-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-2-methyl-tetrahydro-pyran-3-ol