HOLONEOCARZINOSTATIN

Base Information

• Chemical Name: HOLONEOCARZINOSTATIN
• CAS No.: 79633-18-4
• Molecular Formula: C₃₅H₃₃NO₁₂
• Molecular Weight: 659.647
• Mol file: 79633-18-4.mol

Synonyms:Neocarzinostatin chromophore;NCS;Neocarzinostatin Chrom I;Cyclopenta[5,6]cyclonon[1,2-b]oxirene, 1-naphthalenecarboxylic acid deriv.;NCS-Chrom;1-Naphthalenecarboxylic acid, 2-hydroxy-7-methoxy-5-methyl-, (1aS,5R,6R,6aE,9aR)-2,3,8,9-tetradehydro-6-[[2,6-dideoxy-2-(methylamino)-α-D-galactopyranosyl]oxy]-1a,5,6,9a-tetrahydro-1a-[(4R)-2-oxo-1,3-dioxolan-4-yl]cyclopenta[5,6]cyclonon[1,2-b]oxiren-5-yl ester;Neocarzinostatin chromophore I;1-Naphthalenecarboxylic acid, 2-hydroxy-7-methoxy-5-methyl-, 2,3,8,9-tetradehydro-6-[[2,6-dideoxy-2-(methylamino)-α-D-galactopyranosyl]oxy]-1a,5,6,9a-tetrahydro-1a-(2-oxo-1,3-dioxolan-4-yl)cyclopenta[5,6]cyclonon[1,2-b]oxiren-5-yl ester, [1aS-[1aR*(S*),5S*,6S*,6aE,9aS*]]-;

Chemical Property of HOLONEOCARZINOSTATIN

Chemical Property:

• Boiling Point: 922.5±65.0 °C(Predicted)
• PKA: 7.80±0.50(Predicted)
• PSA: 174.77000
• Density: 1.54±0.1 g/cm3(Predicted)
• LogP: 1.77830
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Antineoplastic.

Technology Process of HOLONEOCARZINOSTATIN

There total 37 articles about HOLONEOCARZINOSTATIN 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: 49.0%

C47H61NO12Si2 (207124-53-6) → neocarzinostatin chromophore (79633-18-4)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/ja980588y DOI:10.1021/ja012487x

Reference yield:

(2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol (439857-84-8) → neocarzinostatin chromophore (79633-18-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: 100 percent / I₂; tributyltin hydride; 2,2'-azobisisobutyronitrile / 1,2-dimethoxy-ethane / 3 h / 85 °C

3.1: 94 percent / NaHCO₃; p-dioxane / H₂O / 2 h / 23 °C

4.1: 98 percent / NaH / tetrahydrofuran / 0.25 h / 40 °C

5.1: ammonium formate; H₂ / Pd/C / methanol / 1 h / 23 °C

6.1: NaH / CH₂Cl₂ / 0.17 h / 0 °C

6.2: 75 percent / 0.5 h / 23 °C

7.1: 3 Angstroem molecular sieves / 0.17 h / 23 °C

7.2: 51 percent / boron trifluoride diethyl etherate / toluene / -30 °C

8.1: 49 percent / HF*pyridine / tetrahydrofuran / 1 h / 23 °C

With 1,4-dioxane; 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; hydrogen; iodine; tri-n-butyl-tin hydride; ammonium formate; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1021/ja012487x

Reference yield:

Toluene-4-sulfonic acid (2R,3R,4R,5R,6R)-5-azido-6-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (439857-83-7) → neocarzinostatin chromophore (79633-18-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / NaI / 1,2-dimethoxy-ethane / 12 h / 85 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

3.1: 100 percent / I₂; tributyltin hydride; 2,2'-azobisisobutyronitrile / 1,2-dimethoxy-ethane / 3 h / 85 °C

4.1: 94 percent / NaHCO₃; p-dioxane / H₂O / 2 h / 23 °C

5.1: 98 percent / NaH / tetrahydrofuran / 0.25 h / 40 °C

6.1: ammonium formate; H₂ / Pd/C / methanol / 1 h / 23 °C

7.1: NaH / CH₂Cl₂ / 0.17 h / 0 °C

7.2: 75 percent / 0.5 h / 23 °C

8.1: 3 Angstroem molecular sieves / 0.17 h / 23 °C

8.2: 51 percent / boron trifluoride diethyl etherate / toluene / -30 °C

9.1: 49 percent / HF*pyridine / tetrahydrofuran / 1 h / 23 °C

With 1,4-dioxane; 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; hydrogen; iodine; tri-n-butyl-tin hydride; ammonium formate; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1021/ja012487x

upstream raw materials:

C₄₇H₆₁NO₁₂Si₂

(2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol

Toluene-4-sulfonic acid (2R,3R,4R,5R,6R)-5-azido-6-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

(2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran

Refernces

• 1、 Myers,Liang,Hammond,Harrington,Wu,Kuo. "Total synthesis of (+)-neocarzinostatin chromophore [3]". . p. 5319 - 5320. Retrieved 1998.