(11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester

Base Information

• Chemical Name: (11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester
• CAS No.: 72067-14-2
• Molecular Formula: C₁₇H₂₁N₅O₉
• Molecular Weight: 439.382
• Mol file: 72067-14-2.mol

Synonyms:HerbicidinC

Chemical Property of (11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester

Chemical Property:

• PSA: 204.53000
• LogP: -2.61230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester

There total 23 articles about (11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester 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: 48.0%

methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate (1391974-04-1) → herbicidin C (72067-14-2)

Guidance literature:

methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate; With sodium methylate; In methanol; at 20 ℃; for 1.5h; Inert atmosphere;

With hydrogenchloride; In water;

DOI:10.1002/anie.201201826

Reference yield:

methanol (67-56-1) + aureonuclemycin (123970-01-4) → herbicidin C (72067-14-2)

Guidance literature:

With B₁₂-dependent radical S-adenosyl-L-methionine enzyme; herbicidins cluster contain methyltransferases HbcF; In aq. phosphate buffer; at 30 ℃; for 8h; pH=7; Enzymatic reaction;

DOI:10.1021/acs.orglett.9b00066

Reference yield:

herbicidin G (72283-62-6) → herbicidin C (72067-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: coenzyme A; herbicidins cluster contain serine hydrolase HbcH / aq. phosphate buffer / 8 h / 30 °C / pH 7 / Enzymatic reaction

2: herbicidins cluster contain methyltransferases HbcF; B₁₂-dependent radical S-adenosyl-L-methionine enzyme / aq. phosphate buffer / 8 h / 30 °C / pH 7 / Enzymatic reaction

With coenzyme A; B₁₂-dependent radical S-adenosyl-L-methionine enzyme; herbicidins cluster contain methyltransferases HbcF; herbicidins cluster contain serine hydrolase HbcH; In aq. phosphate buffer;

DOI:10.1021/acs.orglett.9b00066

upstream raw materials:

methyl (4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolane-4-carboxylate

(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

(1S)-1-[(4R,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

Downstream raw materials:

aureonuclemycin