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

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 methyl ester
• CAS No.: 365441-13-0
• Molecular Formula: C₂₉H₄₂O₆Si
• Molecular Weight: 514.734
• Mol file: 365441-13-0.mol

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

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

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 methyl ester

There total 6 articles about (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-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%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester (365441-25-4) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

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 methyl ester (365441-13-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; sodium hydride; trifluoroacetic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

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 methyl ester (365441-13-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; sodium hydride; trifluoroacetic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-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:

2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-8-trityloxy-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

(1R,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-ol

(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