(S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate

Base Information

• Chemical Name: (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate
• CAS No.: 1403588-87-3
• Molecular Formula: C₃₈H₄₁N₃O₇
• Molecular Weight: 651.759
• Mol file: 1403588-87-3.mol

Synonyms:(S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate

Chemical Property of (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate

There total 10 articles about (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate 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: 82.0%

(S)-methyl 2-azido-3-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)propanoate → (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate (1403588-87-3)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - -50 ℃; for 4.33333h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ijch.201500087

Reference yield:

methanol (67-56-1) + C37H39N3O7 → (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate (1403588-87-3)

Guidance literature:

With thionyl chloride; In acetone; at 0 - 20 ℃; for 1.58333h; Inert atmosphere;

DOI:10.1039/c2ob26078f

Reference yield:

C37H42O7 → (S)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-pyran-2-yl)-propanoate (1403588-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 24 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 36 h / 0 - 100 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; trichloroisocyanuric acid / acetone / 1.08 h / 0 °C / Inert atmosphere

6: thionyl chloride / acetone / 1.58 h / 0 - 20 °C / Inert atmosphere

With pyridine; thionyl chloride; sodium azide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/c2ob26078f

upstream raw materials:

1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2S)-azido-3-propanol

methanol

1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2R)-ol-3-tert-butyldiphenylsilyloxypropane

1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2S)-azido-3-tert-butyldiphenylsilyloxypropane

Downstream raw materials:

methyl 3C-β-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-L-alanine