(5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylMethoxy)carbonyl]aMino]-L-glycero-hexonic acid tert-Butyl Ester

Base Information

• Chemical Name: (5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylMethoxy)carbonyl]aMino]-L-glycero-hexonic acid tert-Butyl Ester
• CAS No.: 204074-52-2
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 204074-52-2.mol

Synonyms:tert-butyl 2-benzyloxycarbonylamino-4-(2-oxiranyl)butanoate

Chemical Property of (5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylMethoxy)carbonyl]aMino]-L-glycero-hexonic acid tert-Butyl Ester

Chemical Property:

• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

(5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylmethoxy)carbonyl]amino]-L-glycero-hexonicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylmethoxy)carbonyl]amino]-L-glycero-hexonic acid tert-Butyl Ester is a reactant used in the preparation of the two collagen cross-links pyridinoline and deoxypyridinoline.

Technology Process of (5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylMethoxy)carbonyl]aMino]-L-glycero-hexonic acid tert-Butyl Ester

There total 2 articles about (5S)-5,6-Anhydro-2,3,4-trideoxy-2-[[(phenylMethoxy)carbonyl]aMino]-L-glycero-hexonic acid tert-Butyl Ester 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%

tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate (127623-77-2) → tert-butyl 2-benzyloxycarbonylamino-4-(2-oxiranyl)butanoate (204074-52-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In phosphate buffer; 1,2-dichloro-ethane; at 20 ℃; for 12h; pH=8;

DOI:10.1016/S0957-4166(02)00477-9

Reference yield:

Nα-(Benzyloxycarbonyl)-L-lysine tert-butyl ester (112157-39-8) → tert-butyl 2-benzyloxycarbonylamino-4-(2-oxiranyl)butanoate (204074-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNO₂ / acetic acid; H₂O / 4 h / 20 °C

1.2: 27 percent / KOH / methanol

2.1: 80 percent / aq. 3-chloroperoxybenzoic acid / 1,2-dichloro-ethane; aq. phosphate buffer / 12 h / 20 °C / pH 8

With 3-chloro-benzenecarboperoxoic acid; sodium nitrite; In phosphate buffer; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0957-4166(02)00477-9

Reference yield: 80.0%

tert-butyl 2-benzyloxycarbonylamino-4-(2-oxiranyl)butanoate (204074-52-2) → tert-butyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-hydroxyhexanoate (495401-21-3)

Guidance literature:

With lithium bromide; In tetrahydrofuran; acetic acid; at 20 ℃; for 20h;

DOI:10.1016/S0957-4166(02)00477-9

upstream raw materials:

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

Nα-(Benzyloxycarbonyl)-L-lysine tert-butyl ester

Downstream raw materials:

tert-butyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-hydroxyhexanoate

(S)-2-benzyloxycarbonylamino-6-bromo-5-oxohexanoic acid tert-butyl ester

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

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

Refernces