(4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine

Base Information

• Chemical Name: (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine
• CAS No.: 666753-84-0
• Molecular Formula: C₂₁H₁₉Cl₃N₄O₃S
• Molecular Weight: 513.832
• Mol file: 666753-84-0.mol

Synonyms:

Chemical Property of (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine

There total 2 articles about (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine 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:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (666753-83-9) → (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine (666753-84-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.75 h / 0 °C

2: pyridine / CH₂Cl₂ / 0.08 h / 0 °C

3: 4.16 g / (i-Pr)2NEt / CH₂Cl₂ / 3.5 h / 0 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/b309823k

Reference yield:

2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (1053555-47-7) → (4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine (666753-84-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 0.08 h / 0 °C

2: 4.16 g / (i-Pr)2NEt / CH₂Cl₂ / 3.5 h / 0 °C

With pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/b309823k

Reference yield:

(4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine (666753-84-0) → ((2S,3R,4S,5R,6S)-3-Amino-5-azido-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-methanol

Guidance literature:

With acetic acid; at 20 ℃; for 0.5h;

DOI:10.1039/b309823k

upstream raw materials:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

phenyl 4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside