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

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate
• CAS No.: 864875-52-5
• Molecular Formula: C₅₀H₇₃N₉O₁₃
• Molecular Weight: 1008.18

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-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:

(2S,3R,4R,5R,6R)-5-azido-2-(iodomethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol (864875-47-8) → (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate (864875-52-5)

Guidance literature:

Multi-step reaction with 9 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

8: pyridine / CH₂Cl₂

9: NaN₃ / dimethylformamide

With pyridine; palladium diacetate; sodium azide; 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; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5: Heck reaction;

DOI:10.1002/anie.200500892

Reference yield:

(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol (864875-46-7) → (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate (864875-52-5)

Guidance literature:

Multi-step reaction with 11 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

10: pyridine / CH₂Cl₂

11: NaN₃ / dimethylformamide

With pyridine; palladium diacetate; sodium azide; 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; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7: Heck reaction;

DOI:10.1002/anie.200500892

Reference yield:

(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-azido-6-phenoxytetrahydro-2H-pyran-3,4-diyl → (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate (864875-52-5)

Guidance literature:

Multi-step reaction with 12 steps

1: K₂CO₃; MeOH

2: 81 percent / pyridine

3: 91 percent / NaI; n-Bu₄NI / 1,2-dimethoxy-ethane

4: 93 percent / pyridine

5: H₂; Et₃N / Pd/C / ethanol

6: pyridine

7: 86 percent / n-Bu₄NI; CAN / acetonitrile

8: 73 percent / Pd(OAc)2; (o-Tol)3P; Et₃N / acetonitrile / 70 °C

9: Zn; AcOH / tetrahydrofuran

10: HgCl₂; Et₃N / dimethylformamide

11: pyridine / CH₂Cl₂

12: NaN₃ / dimethylformamide

With pyridine; methanol; palladium diacetate; sodium azide; ammonium cerium(IV) nitrate; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; mercury dichloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 8: Heck reaction;

DOI:10.1002/anie.200500892

upstream raw materials:

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

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

(2R,3R,4R,5R,6S)-3-azido-5-hydroxy-6-(iodomethyl)-2-phenoxytetrahydro-2H-pyran-4-yl benzoate

((2R,3R,4R,5R,6R)-5-azido-3,4-dihydroxy-6-phenoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

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

glycocinnasperimicin D

C₆₁H₉₀N₁₀O₂₀

C₆₃H₉₀Cl₃N₉O₂₁

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