(4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
• CAS No.: 804551-93-7
• Molecular Formula: C₂₆H₄₂O₆Si
• Molecular Weight: 478.701
• Mol file: 804551-93-7.mol

Synonyms:(4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

Chemical Property of (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

There total 9 articles about (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-hydroxy-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester (804552-05-4) → (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester (804551-93-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1021/ol0480325

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester (804551-93-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 87 percent / SnCl₄ / CH₂Cl₂ / 12 h / -78 °C

2.1: 2.8 g / SbCl₅ / CH₂Cl₂ / -78 - -50 °C

3.1: 95 percent / Proton Sponge(R); molecular sieves 4 Angstroem / CH₂Cl₂ / 6 h

4.1: O₃ / methanol; CH₂Cl₂ / -78 °C

4.2: Me₂S / methanol; CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: 85 percent / TfOH / CH₂Cl₂ / 24 h / -70 °C

6.1: 80 percent / m-CPBA / CH₂Cl₂ / 12 h / 20 °C

7.1: K₂CO₃ / methanol / 2 h / 20 °C

7.2: 65 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 2 h / 20 °C

8.1: 93 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; trifluorormethanesulfonic acid; 4 A molecular sieve; antimonypentachloride; tin(IV) chloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/ol0480325

Reference yield:

(2R,3S)-4-benzyloxy-3-methoxy-2-methyl-butyraldehyde (804551-90-4) → (4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyldimethyl-silanyloxy)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester (804551-93-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / TfOH / CH₂Cl₂ / 24 h / -70 °C

2.1: 80 percent / m-CPBA / CH₂Cl₂ / 12 h / 20 °C

3.1: K₂CO₃ / methanol / 2 h / 20 °C

3.2: 65 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 2 h / 20 °C

4.1: 93 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; trifluorormethanesulfonic acid; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/ol0480325

upstream raw materials:

t-butyldimethylsiyl triflate

(4R,5R,6R)-6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-hydroxy-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

benzyloxyacetoaldehyde

(2R,3S)-4-benzyloxy-3-methoxy-2-methyl-butyraldehyde

Downstream raw materials:

[(2S,4S,5S,6S)-6-((1S,2S)-3-Benzyloxy-2-methoxy-1-methyl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(4R,5R,6R)-1-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-diazo-ethanone

(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester