(S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate

Base Information

• Chemical Name: (S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate
• CAS No.: 82689-20-1
• Molecular Formula: C19H30N2O5
• Molecular Weight: 366.458
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70448233
• Nikkaji Number: J1.170.617G
• Wikidata: Q82267207
• Mol file: 82689-20-1.mol

Synonyms:82689-20-1;Boc-Lysinol(Z);(S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate;BOC-L-LYS(Z)-OL;benzyl N-[(5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]carbamate;N-alpha-t-Butyloxycarbonyl-N-epsilon-benzyloxycarbonyl-L-lysinol;MFCD00235934;N-ALPHA-BOC-N-EPSILON-CBZ-L-LYSINOL;SCHEMBL8838459;DTXSID70448233;AKOS016843332;DS-3739;CS-0154483;A864366;Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)(S)-dicarbamate;Benzyl tert-butyl [(5S)-6-hydroxyhexane-1,5-diyl]biscarbamate;benzyl (5S)-5-{[t-butyloxycarbonyl]amino}-6-hydroxyhexylcarbamate;benzyl(5S)-5-{[t-butyloxycarbonyl]amino}-6-hydroxyhexylcarbamate;benzyl{(5S)-5-[(tert-butoxycarbonyl)amino]-6-hydroxyhexyl}carbamate;(S)-6-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-1-hexanol;benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate

Chemical Property of (S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate

Chemical Property:

• Melting Point: 62-63℃
• Boiling Point: 551.4±50.0 °C(Predicted)
• PKA: 12.06±0.46(Predicted)
• PSA: 96.89000
• Density: 1.122±0.06 g/cm3(Predicted)
• LogP: 3.75050
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 366.21547206
• Heavy Atom Count: 26
• Complexity: 417

Purity/Quality:

99% ^*data from raw suppliers

Boc-Lysinol(Z) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCCCNC(=O)OCC1=CC=CC=C1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)CO
• Uses: Boc-Lysinol(Z) is used to prepare N-(iminoethyl)lysinol derivs. as nitric oxide synthase inhibitors.

Technology Process of (S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate

There total 8 articles about (S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate 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: 96.0%

Boc-L-Lys(Z)-OMe (73548-77-3) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-L-lysinol (82689-20-1,252940-35-5)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 48h;

DOI:10.1002/ejoc.201500144

Reference yield: 92.0%

Boc-Lys(Z)-OH (2389-45-9) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-L-lysinol (82689-20-1,252940-35-5)

Guidance literature:

Boc-Lys(Z)-OH; With 4-methyl-morpholine; isobutyl chloroformate;

With sodium tetrahydroborate;

DOI:10.1016/j.tetasy.2015.09.012

Reference yield:

aqueous sodium chloride + Boc-L-Lys(Z)-OMe (73548-77-3) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-L-lysinol (82689-20-1,252940-35-5)

Guidance literature:

With sodium borohydrid; lithium chloride; In tetrahydrofuran; ethanol; water;

upstream raw materials:

Boc-L-Lys(Z)-OMe

C₂₄H₃₆N₂O₈

Boc-Lys(Z)-OH

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

Downstream raw materials:

Methanesulfonic acid (S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexyl ester

[5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hexyl]-carbamic acid benzyl ester

((Z)-(S)-5-tert-Butoxycarbonylamino-8-hydroxy-oct-6-enyl)-carbamic acid benzyl ester

((5S,6S)-5-tert-Butoxycarbonylamino-6,8-dihydroxy-octyl)-carbamic acid benzyl ester

Refernces

• 1、 Baldwin, Christopher R.,Birmingham, William R.,Flitsch, Sabine L.,Ford, Grayson J.,Hepworth, Lorna J.,Huang, Min,Kress, Nico,Marshall, James R.,Mattey, Ashley P.,Seibt, Lisa S.,Turner, Nicholas J.. "Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades". supporting information. p. 7949 - 7952. Retrieved 2020/09/09.
• 2、 Ghosh, Subrata K.,Ganzmann, Carola,Gladysz, John A.. "Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis". . p. 1273 - 1280. Retrieved 2015/11/09.