(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide
• CAS No.: 365441-09-4
• Molecular Formula: C₃₀H₄₅NO₆Si
• Molecular Weight: 543.776
• Mol file: 365441-09-4.mol

Synonyms:(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide

Chemical Property of (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide

There total 7 articles about (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide 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: 98.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester (365441-13-0) → (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide (365441-09-4)

Guidance literature:

With trimethylaluminum; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

benzyl bromide (100-39-0) → (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide (365441-09-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / NaH / dimethylformamide / 1.5 h / 20 °C

2: TFA / 1 h / 0 °C

3: BF₃*OEt₂ / acetonitrile / 2 h / 0 °C

4: 5M aq. NaOH / methanol / 2 h / Heating

5: HCl / 5 h / Heating

6: 97 percent / imidazole / dimethylformamide / 1 h / 20 °C

7: 98 percent / Me₃Al / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; trimethylaluminum; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7: Weinreb procedure;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose (65190-43-4) → (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide (365441-09-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / NaH / dimethylformamide / 1.5 h / 20 °C

2: TFA / 1 h / 0 °C

3: BF₃*OEt₂ / acetonitrile / 2 h / 0 °C

4: 5M aq. NaOH / methanol / 2 h / Heating

5: HCl / 5 h / Heating

6: 97 percent / imidazole / dimethylformamide / 1 h / 20 °C

7: 98 percent / Me₃Al / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; trimethylaluminum; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7: Weinreb procedure;

DOI:10.1016/S0040-4039(01)01069-3

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

benzyl bromide

4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose

Downstream raw materials:

(4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-one