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

Base Information

• Chemical Name: 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal
• CAS No.: 135103-82-1
• Molecular Formula: C₁₆H₂₃N₃O₂S₂
• Molecular Weight: 353.51
• Mol file: 135103-82-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal 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: 80.0%

1.3-propanedithiol (109-80-8) + ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside (135103-81-0) → 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal (135103-82-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.75h; Ambient temperature;

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

Reference yield:

ethyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside (177723-40-9) → 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal (135103-82-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h

With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane;

DOI:10.1080/00397919608003563

Reference yield:

ethyl 6-O-tosyl-2,3-dideoxy-α-D-erythro-pyranoside (177723-39-6) → 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal (135103-82-1)

Guidance literature:

Multi-step reaction with 3 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

3: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h

With sodium azide; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00397919608003563

upstream raw materials:

1.3-propanedithiol

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

benzyl bromide

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

Downstream raw materials:

6-azido-2,3,6-trideoxy-5-acetoxy-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