2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

Base Information

• Chemical Name: 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol
• CAS No.: 207123-37-3
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 207123-37-3.mol

Synonyms:2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

Chemical Property of 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

There total 27 articles about 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol 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: 96.0%

2,5-anhydro-1,3,4,6-tetradeoxy-7-O-<(1,1-dimethylethyl)diphenylsilyl>-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol (221546-67-4) → 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol (207123-37-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo982205k

Reference yield: 92.0%

[(R)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethyl]-carbamic acid benzyl ester (207123-36-2) → 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol (207123-37-3)

Guidance literature:

With water; ammonium chloride; zinc; In methanol; at 80 ℃;

DOI:10.1039/a800727f

Reference yield:

L-xylose (609-06-3) → 2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol (207123-37-3)

Guidance literature:

Multi-step reaction with 15 steps

1: HCl / 5 - 10 °C

2: pyridine / 24 h

3: 1.) acetic acid, acetic anhydride, H₂SO₄, 2.) BF₃*OEt₂ / 1.) room temperature, overnight, 2.) CH₂Cl₂, 0 deg C, 36 h

4: 99 percent / K₂CO₃ / tetrahydrofuran; methanol / 0.33 h

5: 89 percent / p-toluenesulfonic acid monohydrate / 1.5 h

6: 95 percent / 1,3-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

7: 96 percent / camphorsulfonic acid / methanol / 3.5 h

8: 75 percent / tributylphosphine / tetrahydrofuran / 1.5 h

9: 42 percent / Ph₃SnH, azobis(isobutyronitrile) / toluene / 2 h / Heating

10: LiAlH₄ / tetrahydrofuran

11: 236.0 mg / imidazole / tetrahydrofuran / 6 h

12: camphorsulfonic acid, hydrogen / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

13: 171.5 mg / NaHCO₃ / tetrahydrofuran; H₂O

14: 64 percent / triphenylphosphine, iodomethane, imidazole / toluene / 22 h / Heating

15: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triphenylstannane; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo982205k

upstream raw materials:

[(R)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethyl]-carbamic acid benzyl ester

2,5-anhydro-1,3,4,6-tetradeoxy-7-O-<(1,1-dimethylethyl)diphenylsilyl>-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

L-xylose

(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol

Downstream raw materials:

[(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester