(5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester

Base Information

• Chemical Name: (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester
• CAS No.: 152426-92-1
• Molecular Formula: C₃₈H₆₄O₉S₂Si
• Molecular Weight: 757.138

Synonyms:(5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester

Chemical Property of (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester

There total 23 articles about (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid 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: 90.0%

(6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one (297135-61-6) → (S)-6-[(S)-3-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-dihydro-pyran-2,4-dione + (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester (152426-92-1)

Guidance literature:

With ethanol; In toluene; Heating;

DOI:10.1016/S0040-4039(00)74063-9

Reference yield:

[(2R,3R)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-methanol (121352-88-3) → (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester (152426-92-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / Red-Al / toluene

2: 98 percent / imidazole

3: 98 percent / H₂ / Pd-black / ethanol

4: 92 percent / Swern oxidation

5: 84 percent / MgBr₂*OEt₂ / diethyl ether

6: 1) t-BuLi, HMPA / 1) THF, -78 deg C

7: 92 percent / PPTS / methanol

8: 91 percent / SO₃*pyridine, DMSO, NEt₃

9: 1) LDA, 2) LiI

10: 90 percent / toluene / Heating

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; magnesium bromide; lithium iodide; lithium diisopropyl amide; palladium; In methanol; diethyl ether; ethanol; toluene;

DOI:10.1016/S0040-4039(00)74063-9

Reference yield:

[(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene (187527-29-3) → (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester (152426-92-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / H₂ / Pd-black / ethanol

2: 92 percent / Swern oxidation

3: 84 percent / MgBr₂*OEt₂ / diethyl ether

4: 1) t-BuLi, HMPA / 1) THF, -78 deg C

5: 92 percent / PPTS / methanol

6: 91 percent / SO₃*pyridine, DMSO, NEt₃

7: 1) LDA, 2) LiI

8: 90 percent / toluene / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; magnesium bromide; lithium iodide; lithium diisopropyl amide; palladium; In methanol; diethyl ether; ethanol; toluene;

DOI:10.1016/S0040-4039(00)74063-9

upstream raw materials:

ethanol

(6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one

(2S,4'R)-2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-2,3-dihydro-4H-pyran-4-one

[(2R,3R)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-methanol

Downstream raw materials:

{(4R,6R)-6-[(S)-3-[2-((2S,6R)-6-Benzyloxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid ethyl ester

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