(6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate

Base Information

• Chemical Name: (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate
• CAS No.: 165674-17-9
• Molecular Formula: C₃₂H₄₄BrNO₁₀Si
• Molecular Weight: 710.692
• Mol file: 165674-17-9.mol

Synonyms:(6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate

Chemical Property of (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate

There total 10 articles about (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate 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:

2,3-Isopropylidene-D-gulono-γ-lactone (23843-32-5) → (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate (165674-17-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole

2: DIBAL / -78 °C

4: DIEA

5: HF, Py

6: TPAP, NMO

7: NaClO₂, KH₂PO₄

8: Ph₃P, DEAD

With pyridine; 1H-imidazole; sodium chlorite; potassium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen fluoride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;

DOI:10.1021/ja00132a047

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate (165674-17-9)

Guidance literature:

Multi-step reaction with 6 steps

2: DIEA

3: HF, Py

4: TPAP, NMO

5: NaClO₂, KH₂PO₄

6: Ph₃P, DEAD

With pyridine; sodium chlorite; potassium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;

DOI:10.1021/ja00132a047

Reference yield:

(4R,5R)-5-[(1R,2R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde → (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-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)propanoate (165674-17-9)

Guidance literature:

Multi-step reaction with 6 steps

2: DIEA

3: HF, Py

4: TPAP, NMO

5: NaClO₂, KH₂PO₄

6: Ph₃P, DEAD

With pyridine; sodium chlorite; potassium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;

DOI:10.1021/ja00132a047

upstream raw materials:

6-bromopiperonyl alcohol

(2S,3R)-3-<(4S,5R)-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)propanoic acid

2,3-Isopropylidene-D-gulono-γ-lactone

O-benzylhydoxylamine hydrochloride

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

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

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

(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