(3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one
• CAS No.: 157219-96-0
• Molecular Formula: C₂₅H₄₀O₄S₂Si
• Molecular Weight: 496.808

Synonyms:(3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

Chemical Property of (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

Chemical Property:

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Safty Information:

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Technology Process of (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

There total 16 articles about (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one 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%

t-butyldimethylsiyl triflate (69739-34-0) + (3R,4R,5R)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-hydroxy-3-methyl-dihydro-furan-2-one (157219-95-9) → (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one (157219-96-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/jo990988j

Reference yield: 98.0%

tert-butyldiphenylsilyl triflate (92886-86-7) + (3R,4R,5R)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-hydroxy-3-methyl-dihydro-furan-2-one (157219-95-9) → (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one (157219-96-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00083a008

Reference yield:

(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (109958-35-2) → (3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one (157219-96-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

3.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

4.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

5.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

6.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Reduction / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Methylation / 8.1: Metallation / 9.1: Ring cleavage / 10.1: Etherification;

DOI:10.1021/jo990988j

upstream raw materials:

tert-butyldiphenylsilyl triflate

(3R,4R,5R)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-hydroxy-3-methyl-dihydro-furan-2-one

t-butyldimethylsiyl triflate

(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

(E)-(4R,5S)-5-Benzyloxy-5-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-4-methyl-pent-2-enal

(3R,4R,5S)-5-((E)-(1S,2R)-1-Benzyloxy-5-hydroxy-2-methyl-pent-3-enyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

(3R,4R,5S)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-hydroxymethyl-oxiranyl)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

(E)-(4R,5S)-5-Benzyloxy-5-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-4-methyl-pent-2-enoic acid ethyl ester

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