(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate
CAS No.:864875-51-4
Molecular Formula:C₅₀H₇₄N₆O₁₄
Molecular Weight:983.169
Hs Code.:

(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

Synonyms:(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

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Chemical Property of (2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

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Technology Process of (2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

There total 13 articles about (2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate 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: 72.0%

: Benzoic acid (2R,3R,4R,5S,6R)-3-amino-2-[4-((E)-2-{3-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)-amino]-propylcarbamoyl}-vinyl)-phenoxy]-5-hydroxy-6-methyl-tetrahydro-pyran-4-yl ester

: 322474-21-5
N,N'-bis-Boc-S-methyl-isothiourea

: 864875-51-4
(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

Guidance literature:: With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
DOI:10.1002/chem.200901745

Reference yield:

: 864875-47-8
(2S,3R,4R,5R,6R)-5-azido-2-(iodomethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol

: 864875-51-4
(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / pyridine

2: H₂; Et₃N / Pd/C / ethanol

3: pyridine

4: 86 percent / n-Bu₄NI; CAN / acetonitrile

5: 73 percent / Pd(OAc)2; (o-Tol)3P; Et₃N / acetonitrile / 70 °C

6: Zn; AcOH / tetrahydrofuran

7: HgCl₂; Et₃N / dimethylformamide

With pyridine; palladium diacetate; ammonium cerium(IV) nitrate; hydrogen; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; tris-(o-tolyl)phosphine; mercury dichloride; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 5: Heck reaction;
DOI:10.1002/anie.200500892

Reference yield:

: 864875-46-7
(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol

: 864875-51-4
(2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / pyridine

2: 91 percent / NaI; n-Bu₄NI / 1,2-dimethoxy-ethane

3: 93 percent / pyridine

4: H₂; Et₃N / Pd/C / ethanol

5: pyridine

6: 86 percent / n-Bu₄NI; CAN / acetonitrile

7: 73 percent / Pd(OAc)2; (o-Tol)3P; Et₃N / acetonitrile / 70 °C

8: Zn; AcOH / tetrahydrofuran

9: HgCl₂; Et₃N / dimethylformamide

With pyridine; palladium diacetate; ammonium cerium(IV) nitrate; hydrogen; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; mercury dichloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; acetonitrile; 7: Heck reaction;
DOI:10.1002/anie.200500892