phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside
• CAS No.: 832738-42-8
• Molecular Formula: C₄₃H₅₆Cl₃NO₈S
• Molecular Weight: 854.334

Synonyms:phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

Chemical Property of phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

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Technology Process of phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

There total 4 articles about phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside 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: 72.0%

phenyl 4,6-O-benzylidene-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-13C)glucopyranoside (832738-41-7) → phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-13C)glucopyranoside (832738-42-8)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; for 0.5h;

DOI:10.1039/b410544c

Reference yield:

C18(13)CH21NO4S → phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-13C)glucopyranoside (832738-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / tetrahydrofuran / 2.5 h / 20 °C

2: 86 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; DMAP / CHCl₃ / 12 h / 20 °C

3: 72 percent / NaBH₃CN; HCl / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; chloroform;

DOI:10.1039/b410544c

Reference yield:

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-(1-13C)glucopyranoside → phenyl 6-O-benzyl-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-13C)glucopyranoside (832738-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. PPh₃ / tetrahydrofuran / 17 h / 20 °C

2: 2,6-lutidine / tetrahydrofuran / 2.5 h / 20 °C

3: 86 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; DMAP / CHCl₃ / 12 h / 20 °C

4: 72 percent / NaBH₃CN; HCl / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In tetrahydrofuran; chloroform;

DOI:10.1039/b410544c

upstream raw materials:

phenyl 4,6-O-benzylidene-3-O-((R)-3-(benzyloxy)tetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

phenyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-¹³C)glucopyranoside

Downstream raw materials:

C₅₂⁽¹³⁾CH₆₆Cl₃NO₁₅P₂

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