Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

Base Information

Chemical Name:Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester
CAS No.:183268-63-5
Molecular Formula:C₂₈H₃₄O₁₁S
Molecular Weight:578.637
Hs Code.:

Synonyms:Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

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Chemical Property of Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

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Technology Process of Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

There total 7 articles about Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl 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: 80.0%

: 124-63-0
methanesulfonyl chloride

: 183268-61-3
Acetic acid (1S,2S,3R,4S,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-hydroxy-cyclohexyl ester

: 183268-63-5
Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

Guidance literature:: In pyridine; at 0 ℃; for 0.166667h;
DOI:10.1021/jo9607828

Reference yield:

: 135735-90-9
(1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol

: 183268-63-5
Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / Me₃NO, OsO₄ / 2-methyl-propan-2-ol; pyridine; H₂O / 12 h / Heating

2: 90 percent / DMAP / triethylamine / 3 h / Heating

3: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

4: 1.) Et₃N, SOCl₂, 2.) NaIO₄, RuCl₃*H₂O / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) CCl₄, CH₃CN, H₂O, 0 deg C, 1 h

5: 2.) 10percent H₂SO₄ / 1.) DMF, room temperature, 6 h, 2.) THF, 2 h

6: 80 percent / pyridine / 0.17 h / 0 °C

With dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; trimethylamine-N-oxide; sulfuric acid; water; triethylamine; trifluoroacetic acid; In pyridine; dichloromethane; water; triethylamine; tert-butyl alcohol;
DOI:10.1021/jo9607828

Reference yield:

: 171252-92-9
(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

: 183268-63-5
Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 14 percent / Me₃NO, pyridine, H₂O, OsO₄ / 2-methyl-propan-2-ol / 48 h / Heating

2: 1.) Et₃N, SOCl₂, 2.) NaIO₄, RuCl₃*H₂O / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) CCl₄, CH₃CN, H₂O, 0 deg C, 1 h

3: 2.) 10percent H₂SO₄ / 1.) DMF, room temperature, 6 h, 2.) THF, 2 h

4: 80 percent / pyridine / 0.17 h / 0 °C

With pyridine; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; trimethylamine-N-oxide; sulfuric acid; water; triethylamine; In pyridine; tert-butyl alcohol;
DOI:10.1021/jo9607828