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

Base Information

• Chemical Name: (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone
• CAS No.: 441353-26-0
• Molecular Formula: C₁₄H₁₆INO₄
• Molecular Weight: 389.19
• Mol file: 441353-26-0.mol

Synonyms:(2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone

Chemical Property of (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone

There total 5 articles about (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone 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: 39.0%

(2S)-2-([(benzyloxy)carbonyl]amino)hex-5-enoic acid (182422-50-0) → (2S,5S)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone (441353-27-1) + (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone (441353-26-0)

Guidance literature:

With iodine; sodium hydrogencarbonate; potassium iodide; In dichloromethane; at 0 ℃; for 48h;

DOI:10.1016/S0957-4166(03)00400-2

Reference yield:

tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate (127623-77-2) → (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone (441353-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / aq. trifluoroacetic acid / 1 h / 20 °C

2: 39 percent / aq. NaHCO₃; I₂; KI / CH₂Cl₂ / 48 h / 0 °C

With iodine; sodium hydrogencarbonate; trifluoroacetic acid; potassium iodide; In dichloromethane;

DOI:10.1016/S0957-4166(03)00400-2

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,5R)-2-benzyloxycarbonylamino-5-iodomethyl-δ-valerolactone (441353-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dioxane; H₂O / 2.5 h / 20 °C

2: 98 percent / aq. trifluoroacetic acid / 1 h / 20 °C

3: 39 percent / aq. NaHCO₃; I₂; KI / CH₂Cl₂ / 48 h / 0 °C

With iodine; sodium hydrogencarbonate; trifluoroacetic acid; potassium iodide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0957-4166(03)00400-2

upstream raw materials:

(2S)-2-([(benzyloxy)carbonyl]amino)hex-5-enoic acid

tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate

benzyl chloroformate

tert-butyl (2S)-2-aminohex-5-enoate

Downstream raw materials:

allyl (2S,5R)-2-benzyloxycarbonylamino-5-hydroxy-6-iodohexanoate

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

4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-(allyloxycarbonyl)-2-hydroxypentyl]-3-pyridiniumolate