6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose

Base Information

• Chemical Name: 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose
• CAS No.: 832738-53-1
• Molecular Formula: C₃₃H₄₄Cl₃NO₉
• Molecular Weight: 706.062

Synonyms:6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose

Chemical Property of 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose

Chemical Property:

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Technology Process of 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose

There total 5 articles about 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-¹³C)glucopyranose 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: 83.0%

phenyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-(1-13C)glucopyranoside (832738-52-0) → 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-13C)glucopyranose (832738-53-1)

Guidance literature:

With N-Bromosuccinimide; In acetone;

DOI:10.1039/b410544c

Reference yield:

C18(13)CH21NO4S → 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-13C)glucopyranose (832738-53-1)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 93 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; DMAP / CHCl₃ / 0.33 h / 20 °C

3: 84 percent / NaBH₃CN; HCl / tetrahydrofuran

4: 83 percent / aq. NBS / acetone

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

DOI:10.1039/b410544c

Reference yield:

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-(1-13C)glucopyranoside → 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-(1-13C)glucopyranose (832738-53-1)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 93 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; DMAP / CHCl₃ / 0.33 h / 20 °C

4: 84 percent / NaBH₃CN; HCl / tetrahydrofuran

5: 83 percent / aq. NBS / acetone

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

DOI:10.1039/b410544c

upstream raw materials:

phenyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-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

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

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