Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
CAS No.:73143-50-7
Molecular Formula:C₃₇H₄₄O₁₅S₃
Molecular Weight:824.945
Hs Code.:

Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl 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:

: 73143-43-8
(4S,5R)-4-O,5-O-cyclohexylidene-4,5-dihydroxycyclohex-2-en-1-one

: 73143-50-7
Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / hydrogen / 10percent Pd/C / ethyl acetate

2: lithium borohydride / bis-(2-methoxy-ethyl) ether

3: acid

4: selective p-toluenesulfonylation

5: boron trifluoride etherate / 1,2-dichloro-ethane

6: reduction

With lithium borohydride; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In diethylene glycol dimethyl ether; ethyl acetate; 1,2-dichloro-ethane;
DOI:10.1021/ja00522a077

Reference yield:

: 69240-09-1
2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

: 73143-50-7
Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: boron trifluoride etherate / 1,2-dichloro-ethane

2: reduction

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane;
DOI:10.1021/ja00522a077

Reference yield:

: 73209-16-2
(1S,2R,4R)-cyclohexane-1,2,4-triol

: 73143-50-7
Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: selective p-toluenesulfonylation

2: boron trifluoride etherate / 1,2-dichloro-ethane

3: reduction

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane;
DOI:10.1021/ja00522a077