Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester

Base Information

• Chemical Name: Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester
• CAS No.: 236387-97-6
• Molecular Formula: C₃₀H₃₁N₃O₁₀S
• Molecular Weight: 625.656
• Mol file: 236387-97-6.mol

Synonyms:Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester

Chemical Property of Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester

There total 16 articles about Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) 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: 60.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (7R)-7-((1R)<(5S,4R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>(methoxymethoxy)methyl)-8-hydroxy-2H-1,3-dioxoleno<4,5-g>isochroman-5-one (236387-96-5) → Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester (236387-97-6)

Guidance literature:

With dmap; In 1,2-dichloro-ethane; for 4h; Ambient temperature;

DOI:10.1021/jo9902042

Reference yield:

(4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime (165674-19-1) → Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester (236387-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 0.5 h / -50 - 20 °C

2: 60 percent / DMAP / 1,2-dichloro-ethane / 4 h / Ambient temperature

With dmap; sodium tetrahydroborate; In methanol; 1,2-dichloro-ethane;

DOI:10.1021/jo9902042

Reference yield:

6-((2S,3R)-3-<(5S,4R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(methoxymethoxy)-2-(1,1,2,2-tetramethyl-1-silapropoxy)propanoyl)-2H-benzo-1,3-dioxolane-5-carbaldehyde (165674-18-0) → Imidazole-1-carbothioic acid O-((R)-7-{(R)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-oxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl) ester (236387-97-6)

Guidance literature:

Multi-step reaction with 4 steps

1: HF*pyridine / tetrahydrofuran; pyridine / 24 h / Ambient temperature

2: Dess-Martin reagent / CH₂Cl₂ / 3 h / Ambient temperature

3: NaBH₄ / methanol / 0.5 h / -50 - 20 °C

4: 60 percent / DMAP / 1,2-dichloro-ethane / 4 h / Ambient temperature

With dmap; sodium tetrahydroborate; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo9902042

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

(7R)-7-((1R)<(5S,4R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>(methoxymethoxy)methyl)-8-hydroxy-2H-1,3-dioxoleno<4,5-g>isochroman-5-one

(4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime

6-((2S,3R)-3-<(5S,4R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(methoxymethoxy)-2-(1,1,2,2-tetramethyl-1-silapropoxy)propanoyl)-2H-benzo-1,3-dioxolane-5-carbaldehyde

Downstream raw materials:

(12aS,4R,12R,11bR,3aR,4aR)-4-(methoxymethoxy)-2,2-dimethyl-12-<(phenylmethoxy)amino>-4,12,11b,12a,3a,4a-hexahydro-9H-1,3-dioxoleno<4,5-7',6'>isochromano<4',3'-5,4>benzo<4,5-d>-1,3-dioxolan-6-one