(R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane

Base Information

• Chemical Name: (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane
• CAS No.: 609355-69-3
• Molecular Formula: C₂₅H₃₄O₅
• Molecular Weight: 414.542

Synonyms:(R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane

Chemical Property of (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane

There total 11 articles about (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane 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: 67.0%

chloromethyl methyl ether (107-30-2) + (1R,2R,4R)-2,6-Bis-benzyloxy-4-methyl-1-(R)-oxiranyl-hexan-1-ol (609355-75-1) → (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane (609355-69-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(03)01553-3

Reference yield:

benzyl bromide (100-39-0) → (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane (609355-69-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: NaBO₃*4H₂O / dimethylformamide

2.3: NaH / dimethylformamide / 0 - 20 °C

3.1: 70 percent / p-TsOH / methanol; CH₂Cl₂ / 20 °C

4.1: IBX; DMSO / 20 °C

4.2: 90 percent / KOt-Bu / tetrahydrofuran / 0 °C

5.1: 83 percent / AD mix-β; CH3SO2NH2; OsO4 / 2-methyl-propan-2-ol; H2O / 20 °C

6.1: PhCH(OMe)2; CSA / CH₂Cl₂ / 20 °C

6.2: LiAlH₄ / tetrahydrofuran / 0 °C

6.3: 76 percent / p-TsOH / methanol / 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

8.1: K₂CO₃ / ethanol / 20 °C

9.1: 67 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

With dmap; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; methanesulfonamide; benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01553-3

Reference yield:

2(S)-methyl-(R)-(-)-γ-trityloxymethyl-γ-butyrolactone (180062-86-6) → (R)-2-((1R,2R,4R)-2,6-Bis-benzyloxy-1-methoxymethoxy-4-methyl-hexyl)-oxirane (609355-69-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: DIBALH / CH₂Cl₂ / -78 °C

1.2: 53 percent / NaHMDS / tetrahydrofuran / 0 °C

2.1: NaH / dimethylformamide / 0 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 20 °C

3.2: NaBO₃*4H₂O / dimethylformamide

3.3: NaH / dimethylformamide / 0 - 20 °C

4.1: 70 percent / p-TsOH / methanol; CH₂Cl₂ / 20 °C

5.1: IBX; DMSO / 20 °C

5.2: 90 percent / KOt-Bu / tetrahydrofuran / 0 °C

6.1: 83 percent / AD mix-β; CH3SO2NH2; OsO4 / 2-methyl-propan-2-ol; H2O / 20 °C

7.1: PhCH(OMe)2; CSA / CH₂Cl₂ / 20 °C

7.2: LiAlH₄ / tetrahydrofuran / 0 °C

7.3: 76 percent / p-TsOH / methanol / 20 °C

8.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

9.1: K₂CO₃ / ethanol / 20 °C

10.1: 67 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

With dmap; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; methanesulfonamide; benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.2: Wittig methylenation / 6.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01553-3

upstream raw materials:

chloromethyl methyl ether

(1R,2R,4R)-2,6-Bis-benzyloxy-4-methyl-1-(R)-oxiranyl-hexan-1-ol

benzyl bromide

2(S)-methyl-(R)-(-)-γ-trityloxymethyl-γ-butyrolactone

Downstream raw materials:

(2R,3S,4R,6R)-4,8-Bis-benzyloxy-1-[2-((1S,3R)-1,3-dimethyl-4-triisopropylsilanyloxy-butyl)-[1,3]dithian-2-yl]-3-methoxymethoxy-6-methyl-octan-2-ol

(2S,3R)-5-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-2-((1R,3R)-1,5-bis-benzyloxy-3-methyl-pentyl)-5-methoxy-tetrahydro-furan-3-ol

(2S,3R,5S,8R,10S)-2-((1R,3R)-1,5-Bis-benzyloxy-3-methyl-pentyl)-3-hydroxy-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

(2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol

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