(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol
• CAS No.: 675876-42-3
• Molecular Formula: C₁₉H₂₁N₃O₄S
• Molecular Weight: 387.459
• Mol file: 675876-42-3.mol

Synonyms:(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol

There total 8 articles about (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol 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: 47.0%

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside (1226524-10-2) → phenyl 2-azido-6-O-benzyl-2-deoxy-1-thio-β-D-galactopyranoside + (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol (675876-42-3)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2012.07.003

Reference yield:

[(2R,3S,4R,5R,6S)-5-Azido-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-methanol → (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol (675876-42-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/j.tetlet.2003.12.042

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol (675876-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1: CSA / dimethylformamide; methanol / 80 °C

2: imidazole / dimethylformamide; methanol

3: BH₃*THF; Bu₂BOTf

4: aq. HF / acetonitrile

With 1H-imidazole; borane-THF; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen fluoride; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2003.12.042

upstream raw materials:

benzaldehyde dimethyl acetal

phenyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Downstream raw materials:

(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-triethylsilanyloxymethyl-tetrahydro-pyran-4-ol

(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4R,5R,6S)-5-azido-3-benzyloxy-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester