ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside
• CAS No.: 135103-81-0
• Molecular Formula: C₁₅H₂₁N₃O₃
• Molecular Weight: 291.35
• Mol file: 135103-81-0.mol

Synonyms:ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside

Chemical Property of ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside

There total 3 articles about ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside 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: 100.0%

benzyl bromide (100-39-0) + ethyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside (177723-40-9) → ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside (135103-81-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1) 0 deg C 2) 2 h, r.t.;

DOI:10.1016/S0040-4039(00)85991-2

Reference yield:

ethyl 6-O-tosyl-2,3-dideoxy-α-D-erythro-pyranoside (177723-39-6) → ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside (135103-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaN₃ / dimethylformamide / 5 h / 60 °C

2: 1.) NaH, 2.) Bu₄NI / 1.) THF, paraffin oil, 15 min, 2.) THF, paraffin oil, room temperature, 2 h

With sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1080/00397919608003563

Reference yield:

(2R,3S,6S)-6-ethoxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol (23339-16-4) → ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside (135103-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / pyridine

2: 95 percent / NaN₃ / dimethylformamide / 5 h / 60 °C

3: 1.) NaH, 2.) Bu₄NI / 1.) THF, paraffin oil, 15 min, 2.) THF, paraffin oil, room temperature, 2 h

With pyridine; sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1080/00397919608003563

upstream raw materials:

benzyl bromide

ethyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside

ethyl 6-O-tosyl-2,3-dideoxy-α-D-erythro-pyranoside

(2R,3S,6S)-6-ethoxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol

Downstream raw materials:

6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal

methyl (4S,5R)-6-azido-5-hydroxy-4-(phenylmethoxy) hexanoate

(4S,5R)-5-acetoxy-6-azido-4-(phenylmethoxy) hexanal

methyl (4S,5R)-5-acetoxy-6-azido-4-(phenylmethoxy) hexanoate