(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

Base Information

• Chemical Name: (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid
• CAS No.: 309928-96-9
• Molecular Formula: C₁₄H₁₈N₄O₅
• Molecular Weight: 322.321
• Mol file: 309928-96-9.mol

Synonyms:(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

Chemical Property of (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

There total 6 articles about (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 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: 94.0%

(2S,5R)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone (309928-94-7) → (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid (309928-96-9)

Guidance literature:

With caesium carbonate; In methanol; at 20 ℃; for 0.583333h;

DOI:10.1016/S0957-4166(00)00281-0

Reference yield:

methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate (15366-19-5) → (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid (309928-96-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / HBr / acetic acid / -5 °C

2: 86 percent / NaN₃ / dimethylformamide / 1 h / 0 °C

3: NaBH₄ / methanol / 0.33 h / -5 °C

4: 100 percent / CF₃COOH / 0.67 h / 20 °C

5: 94 percent / aq. Cs₂CO₃ / methanol / 0.58 h / 20 °C

With sodium tetrahydroborate; sodium azide; hydrogen bromide; caesium carbonate; trifluoroacetic acid; In methanol; acetic acid; N,N-dimethyl-formamide; 1: Bromination / 2: Substitution / 3: Reduction / 4: Cyclization / 5: Hydrolysis;

DOI:10.1016/S0957-4166(00)00281-0

Reference yield:

(S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone (58456-27-2) → (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid (309928-96-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / NaHCO₃ / 0.17 h / Heating

2: 82 percent / HBr / acetic acid / -5 °C

3: 86 percent / NaN₃ / dimethylformamide / 1 h / 0 °C

4: NaBH₄ / methanol / 0.33 h / -5 °C

5: 100 percent / CF₃COOH / 0.67 h / 20 °C

6: 94 percent / aq. Cs₂CO₃ / methanol / 0.58 h / 20 °C

With sodium tetrahydroborate; sodium azide; hydrogen bromide; sodium hydrogencarbonate; caesium carbonate; trifluoroacetic acid; In methanol; acetic acid; N,N-dimethyl-formamide; 1: methanolysis / 2: Bromination / 3: Substitution / 4: Reduction / 5: Cyclization / 6: Hydrolysis;

DOI:10.1016/S0957-4166(00)00281-0

upstream raw materials:

(2S,5R)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone

methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate

(S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone

methyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-oxohexanoate

Downstream raw materials:

(5R)-5-hydroxy-L-lysine

(2S,5R)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone

tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate tert-butyl ester