(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

Base Information

• Chemical Name: (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid
• CAS No.: 58521-49-6
• Molecular Formula: C13H25 N O5
• Molecular Weight: 275.34
• Hs Code.: 29241990
• DSSTox Substance ID: DTXSID80373163
• Nikkaji Number: J258.860I
• Wikidata: Q72510502
• Mol file: 58521-49-6.mol

Synonyms:58521-49-6;BOC-STA-OH;Boc-statine;(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid;(3S,4S)-3-hydroxy-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoic acid;N-(t-butyloxycarbonyl)-statine;SCHEMBL6519145;DTXSID80373163;KJIQRHBVNGRPCO-UWVGGRQHSA-N;(3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid;MFCD00063180;(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoicacid;AKOS016011217;CS-W010082;BS-42278;E79082;(3S,4S)-3-Hydroxy-4-Boc-amino-6-methyl-heptanoic acid;4(S)-t-butoxycarbonylamino-3(S)-hydroxy-6-methylheptanoic acid;(3S,4S)-6-methyl-4-t-butoxycarbonylamino-3-hydroxyheptanoic acid;Heptanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-6-methyl-, (3S,4S)-

Chemical Property of (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 119-122 ºC
• Refractive Index: 1.479
• Boiling Point: 439.98°C at 760 mmHg
• Flash Point: 219.892°C
• PSA: 95.86000
• Density: 1.107g/cm³
• LogP: 2.15230
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 275.17327290
• Heavy Atom Count: 19
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

Boc-Sta-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(CC(=O)O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H]([C@H](CC(=O)O)O)NC(=O)OC(C)(C)C

Technology Process of (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

There total 69 articles about (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic 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: 99.0%

(3S,4S)-4-(tert-butoxycarbonylamino)-6-methyl-1-trimethylsilylhept-1-yn-3-ol (254752-30-2) → (3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid (58521-49-6)

Guidance literature:

(3S,4S)-4-(tert-butoxycarbonylamino)-6-methyl-1-trimethylsilylhept-1-yn-3-ol; With bis(cyclohexanyl)borane; In tetrahydrofuran; at 20 ℃;

With dihydrogen peroxide; sodium hydrogencarbonate; at 20 ℃;

DOI:10.1016/S0040-4020(00)00905-4

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-6-methylheptanonitrile (174145-77-8) → (3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid (58521-49-6)

Guidance literature:

(3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-6-methylheptanonitrile; With hydrogenchloride; In tetrahydrofuran; at 120 ℃; for 12h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1055/s-2003-41049

Reference yield: 90.0%

(4S,5S)-4-hydroxy-5-isobutyl-1-tert-butoxycarbonylpyrrolidin-2-one (116506-77-5,109579-07-9) → (3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid (58521-49-6)

Guidance literature:

With sodium hydroxide; In acetone; for 0.0833333h; Ambient temperature;

upstream raw materials:

(3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate

(S)-4-tert-Butoxycarbonylamino-3-hydroxy-6-methyl-heptanoic acid ethyl ester

di-tert-butyl dicarbonate

(2S,3S)-butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester

Downstream raw materials:

statine

6-tert-butoxycarbonylamino-2-{2-[4-(4-{1-[1-(2-butylcarbamoyl-1-hydroxy-ethyl)-3-methyl-butylcarbamoyl]-2-methyl-butylcarbamoyl}-phenoxy)-benzoylamino]-4-methyl-pentanoylamino}-hexanoic acid propyl ester

(3S,4S)-4-((2S,3S)-2-(4-(4-((S)-((S)-1-(6-(tert-butoxycarbamoyl)-1-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-1-oxohexan-2-ylamino)-1-oxopropan-2-yl)carbamoyl)phenoxy)benzamido)-3-methylpentanamido)-3-hydroxy-6-methylheptanoic acid butylamide

4-(4-(((2S,3S)-1-((3S,4S)-1-(butylamino)-3-hydroxy-6-methyl-1-oxoheptan-4-ylamino)-3-methyl-1-oxopentan-2-yl)carbamoyl)phenoxy)benzoic acid benzyl ester

Refernces

• 1、 Molinski, Tadeusz F.,Reynolds, Kirk A.,Morinaka, Brandon I.. "Symplocin A, a linear peptide from the bahamian cyanobacterium symploca sp. configurational analysis of N, N -dimethylamino acids by chiral-phase HPLC of naphthacyl esters". experimental part. p. 425 - 431. Retrieved 2012/07/13.
• 2、 Soto-Cairoli, Buddy,Soderquist, John A.. "Strict reagent control in the asymmetric allylboration of N-TIPS-α-amino aldehydes with the B-allyl-10-TMS-9-borabicyclo[3.3.2] decanes". supporting information; experimental part. p. 401 - 404. Retrieved 2009/07/04.