(3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester
• CAS No.: 864277-36-1
• Molecular Formula: C₂₃H₂₉NO₉
• Molecular Weight: 463.485
• Mol file: 864277-36-1.mol

Synonyms:(3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Chemical Property of (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

There total 14 articles about (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic 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: 95.0%

(3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (864277-27-0) + benzyl isothiocyanate (3173-56-6) → (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (864277-36-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In benzene; at 50 ℃;

DOI:10.1016/j.tetlet.2005.06.093

Reference yield:

Acetic acid (3R,6R)-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester (864277-16-7) → (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (864277-36-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 100 percent / MeSO2NH2; AD mixβ / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

2.1: 87 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

3.1: 92 percent / K₂CO₃ / methanol / 20 °C

4.1: m-CPBA / CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C / pH 7

4.2: 89 percent / SiO₂

5.1: 85 percent / CSA / CH₂Cl₂ / 0 °C

6.1: 38 percent / H₂ / Pd/C / hexane / 20 °C

7.1: 75 percent / TEMPO; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / pH 7.0

8.1: 80 percent / K₂CO₃ / dimethylformamide / 20 °C

9.1: 85 percent / TBAF / tetrahydrofuran / 20 °C

10.1: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂ / 0 °C

11.1: CH₂Cl₂ / 20 °C

12.1: 90 percent / DIBALH / tetrahydrofuran / -78 °C

13.1: 83 percent / t-BuOOH; Ti(Oi-Pr)4; (+)-diisopropyl tartrate / CH₂Cl₂ / -20 °C

14.1: 95 percent / i-Pr₂NEt / benzene / 50 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; L-(+)-diisopropyl tartrate; pyridine-SO₃ complex; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 11.1: Wittig reaction / 13.1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetlet.2005.06.093

Reference yield:

Acetic acid (3R,6R)-6-(3-benzyloxy-2-hydroxy-2-hydroxymethyl-propyl)-3,6-dihydro-2H-pyran-3-yl ester (864277-17-8) → (3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Benzylcarbamoyloxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (864277-36-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 87 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

2.1: 92 percent / K₂CO₃ / methanol / 20 °C

3.1: m-CPBA / CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C / pH 7

3.2: 89 percent / SiO₂

4.1: 85 percent / CSA / CH₂Cl₂ / 0 °C

5.1: 38 percent / H₂ / Pd/C / hexane / 20 °C

6.1: 75 percent / TEMPO; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / pH 7.0

7.1: 80 percent / K₂CO₃ / dimethylformamide / 20 °C

8.1: 85 percent / TBAF / tetrahydrofuran / 20 °C

9.1: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂ / 0 °C

10.1: CH₂Cl₂ / 20 °C

11.1: 90 percent / DIBALH / tetrahydrofuran / -78 °C

12.1: 83 percent / t-BuOOH; Ti(Oi-Pr)4; (+)-diisopropyl tartrate / CH₂Cl₂ / -20 °C

13.1: 95 percent / i-Pr₂NEt / benzene / 50 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; L-(+)-diisopropyl tartrate; pyridine-SO₃ complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 10.1: Wittig reaction / 12.1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetlet.2005.06.093

upstream raw materials:

(3aS,5aR,7S,8aS,8bS)-7-((2R,3S)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

benzyl isothiocyanate

(3aS,5aR,7S,8aS,8bS)-7-Hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Acetic acid (3R,6R)-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester

Downstream raw materials:

(S)-3-Benzyl-4-[(3aS,5aR,7R,8aS,8bS)-7-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-ylmethyl]-oxazolidin-2-one

(3aS,5aR,7R,8aS,8bS)-7-((S)-3-Benzyl-2-oxo-oxazolidin-4-ylmethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

(S)-3-Benzyl-4-((3aS,5aR,7R,8aS,8bS)-7-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-ylmethyl)-oxazolidin-2-one

(3aS,5aR,7S,8aS,8bS)-7-[(R)-((R)-3-Benzyl-2-oxo-oxazolidin-4-yl)-hydroxy-methyl]-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester