(E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

Base Information

• Chemical Name: (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester
• CAS No.: 114643-51-5
• Molecular Formula: C₂₄H₃₄N₄O₈
• Molecular Weight: 506.556
• Mol file: 114643-51-5.mol

Synonyms:

Chemical Property of (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

There total 4 articles about (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester 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:

(E)-3-[4-((2R,3R,4R,5R,6R)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester (114643-48-0) → (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester (114643-51-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / acetone / 3 h

2: 98 percent

3: 78 percent / NaN₃ / hexamethylphosphoric acid triamide / 20 h / 80 °C

4: NaOMe

With sodium azide; sodium methylate; triethylamine; In N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1016/0008-6215(87)80249-5

Reference yield:

tert-butyl p-<3,6-di-O-benzoyl-2-(tert-butoxycarbonyl)-amino-2-deoxy-α-D-galactopyranosyloxy>cinnamate (114935-39-6) → (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester (114643-51-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent

2: 78 percent / NaN₃ / hexamethylphosphoric acid triamide / 20 h / 80 °C

3: NaOMe

With sodium azide; sodium methylate; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/0008-6215(87)80249-5

Reference yield:

tert-butyl p-<3,6-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2-deoxy-4-methylsulfonyl-α-D-galactopyranosyloxy>cinnamate (114643-49-1) → (E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester (114643-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaN₃ / hexamethylphosphoric acid triamide / 20 h / 80 °C

2: NaOMe

With sodium azide; sodium methylate; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/0008-6215(87)80249-5

upstream raw materials:

tert-butyl p-<4-azido-3,6-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2,4-di-deoxy-α-D-glucopyranosyloxy>cinnamate

(E)-3-[4-((2R,3R,4R,5R,6R)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

tert-butyl p-<3,6-di-O-benzoyl-2-(tert-butoxycarbonyl)-amino-2-deoxy-α-D-galactopyranosyloxy>cinnamate

tert-butyl p-<3,6-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2-deoxy-4-methylsulfonyl-α-D-galactopyranosyloxy>cinnamate

Downstream raw materials:

tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate