[(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 204066-49-9
• Molecular Formula: C₄₄H₈₃NO₁₂Si₃
• Molecular Weight: 902.399
• Mol file: 204066-49-9.mol

Synonyms:

Chemical Property of [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

There total 9 articles about [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl 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:

Benzyloxyacetyl chloride (19810-31-2) → [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204066-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LiHMDS / 1) THF, -78 deg C, 2) THF

2: 1) TiCl₄, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;

DOI:10.1021/jo980023k

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204066-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 2,6-lutidine

2: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, MeOH, -78 deg C, 2) CH₂Cl₂, MeOH

3: 1) TiCl₄, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂

With 2,6-dimethylpyridine; titanium tetrachloride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine;

DOI:10.1021/jo980023k

Reference yield:

2-(trimethylsilyl)-ethoxycarbonyl chloride (20160-60-5) → [(2S,3R,5R,6S,7R)-2-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204066-49-9)

Guidance literature:

Multi-step reaction with 3 steps

2: 1) LiHMDS / 1) THF, -78 deg C, 2) THF

3: 1) TiCl₄, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;

DOI:10.1021/jo980023k

upstream raw materials:

(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexanal

(2-Benzyloxy-acetyl)-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Benzyloxyacetyl chloride

2-(trimethylsilyl)-ethoxycarbonyl chloride

Downstream raw materials:

[(S)-2-Benzyloxy-2-((2R,4R,5R,6R)-4-hydroxy-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-acetyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

[(S)-2-Benzyloxy-2-((2R,5S,6R)-2-methoxy-5,6-dimethyl-4-oxo-tetrahydro-pyran-2-yl)-acetyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

[(S)-2-Benzyloxy-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetyl]-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester