alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-

Base Information

• Chemical Name: alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-
• CAS No.: 81703-97-1
• Molecular Formula: C₁₅H₁₈F₃NO₄
• Molecular Weight: 333.307
• DSSTox Substance ID: DTXSID201133804

Synonyms:DTXSID201133804;alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-;81703-97-1

Chemical Property of alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 333.11879254
• Heavy Atom Count: 23
• Complexity: 399

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OCC2=CC=CC=C2)NC(=O)C(F)(F)F)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)OCC2=CC=CC=C2)NC(=O)C(F)(F)F)O

Technology Process of alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-

There total 4 articles about alpha-L-lyxo-Hexopyranoside, phenylmethyl 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]- 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: 100.0%

benzyl 4-O-acetyl-N-(trifluoroacetyl)-L-daunosamide (81661-49-6) → benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (81703-97-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0008-6215(00)80810-1

Reference yield: 89.0%

methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (73366-86-6) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (81703-97-1)

Guidance literature:

With toluene-4-sulfonic acid; In hexane; Heating;

DOI:10.1039/c39830000305

Reference yield:

4-O-acetyl-N-(trifluoroacetyl)-L-daunosaminyl bromide (81661-48-5) → benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (81703-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / mercuric bromide, yellow mercuric oxide / 1.) 15 min, 0 deg C, 2.) 2 h, room temperature

2: 100 percent / sodium methoxide / methanol

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

DOI:10.1016/S0008-6215(00)80810-1

upstream raw materials:

benzyl 4-O-acetyl-N-(trifluoroacetyl)-L-daunosamide

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

benzyl alcohol

4-O-acetyl-N-(trifluoroacetyl)-L-daunosaminyl bromide

Downstream raw materials:

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

benzyl 4-O-acetyl-N-(trifluoroacetyl)-L-daunosamide

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

C₃₃H₄₀F₉N₃O₁₁

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