(4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 150843-04-2
• Molecular Formula: C₂₂H₃₆O₆Si
• Molecular Weight: 424.61
• Mol file: 150843-04-2.mol

Synonyms:(4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-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)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 9 articles about (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-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: 93.0%

methanol (67-56-1) + (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (150843-03-1) → (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester (150843-04-2)

Guidance literature:

With mercury dichloride;

DOI:10.1016/S0040-4039(00)79162-3

Reference yield:

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1) → (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester (150843-04-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) HCl, 2.) i-Pr₂EtN

2: magnesium monoperoxyphthalate (MMPP)

3: 77 percent / NH₄F, MeOH

4: pyridine

5: NaI / butan-2-one / Heating

6: Bu₃SnH

7: 1.) LDA / 1.) -78 deg C

8: 1.) lithium naphthalenide (LN)

9: 93 percent / HgCl₂

With pyridine; hydrogenchloride; methanol; ammonium fluoride; tri-n-butyl-tin hydride; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine; naphthalen-1-yl-lithium; sodium iodide; mercury dichloride; lithium diisopropyl amide; In butanone;

DOI:10.1016/S0040-4039(00)79162-3

Reference yield:

[(2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol (150843-01-9) → (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester (150843-04-2)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine

2: NaI / butan-2-one / Heating

3: Bu₃SnH

4: 1.) LDA / 1.) -78 deg C

5: 1.) lithium naphthalenide (LN)

6: 93 percent / HgCl₂

With pyridine; tri-n-butyl-tin hydride; naphthalen-1-yl-lithium; sodium iodide; mercury dichloride; lithium diisopropyl amide; In butanone;

DOI:10.1016/S0040-4039(00)79162-3

upstream raw materials:

methanol

(4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

((2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-2-methyl-tetrahydro-pyran-4-yloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

C₃₆H₄₂O₁₁

C₃₈H₄₆O₁₁