Imidazole-1-carbothioic acid O-[(R)-7-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-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-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl] ester
• CAS No.: 236387-99-8
• Molecular Formula: C₃₆H₄₇N₃O₁₀SSi
• Molecular Weight: 741.935
• Mol file: 236387-99-8.mol

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

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

There total 17 articles about Imidazole-1-carbothioic acid O-[(R)-7-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-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:

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-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl] ester (236387-99-8)

Guidance literature:

Multi-step reaction with 4 steps

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

2: imidazole / pentane / 19 h / Ambient temperature

3: 205 mg / NaBH₄ / methanol / 2 h / Ambient temperature

4: DMAP / 1,2-dichloro-ethane / 14 h / Heating

With 1H-imidazole; dmap; sodium tetrahydroborate; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; pentane;

DOI:10.1021/jo9902042

Reference yield:

(7S)-7-((1S)<(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))-2H-1,3-dioxoleno<4,5-g>isochroman-8-one (236387-98-7) → Imidazole-1-carbothioic acid O-[(R)-7-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl] ester (236387-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 205 mg / NaBH₄ / methanol / 2 h / Ambient temperature

2: DMAP / 1,2-dichloro-ethane / 14 h / Heating

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

DOI:10.1021/jo9902042

Reference yield:

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (4S,5S)-5-{(S)-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-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 → Imidazole-1-carbothioic acid O-[(R)-7-{(S)-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methoxymethoxy-methyl}-5-(tert-butyl-dimethyl-silanyloxy)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-8-yl] ester (236387-99-8)

Guidance literature:

With dmap; In 1,2-dichloro-ethane; Yield given;

DOI:10.1021/ja00132a047

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

tert-butyldimethylsilyl chloride

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

(7S)-7-((1S)<(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))-2H-1,3-dioxoleno<4,5-g>isochroman-8-one

Downstream raw materials:

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

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