Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester
CAS No.:143537-21-7
Molecular Formula:C₂₅H₃₆O₈S₂
Molecular Weight:528.688
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

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Chemical Property of Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

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Technology Process of Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

There total 10 articles about Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl 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: 75.0%

: 143537-20-6
Benzoic acid (3R,3aR,4S,6S,6aR)-4,6-bis-acetoxymethyl-2,3-dihydroxy-hexahydro-cyclopenta[b]furan-6a-ylmethyl ester

: 75-08-1
ethanethiol

: 143537-21-7
Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;
DOI:10.1016/0040-4039(92)88092-J

Reference yield:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 143537-21-7
Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / CH₂Cl₂ / 16 h / Ambient temperature

2: 63 percent / LiAlH₄ / tetrahydrofuran / 0 deg C to r.t.

3: 73 percent / pyridine

4: 1) NaIO₄, OsO₄, 2) NaClO₃ / 1) EtOH, water, 2) 70percent EtOH, 45-50 deg C

5: 98 percent / NaIO₄ / aq. ethanol / Ambient temperature

6: 81 percent / NaBH₄ / methanol

7: 88 percent / pyridine

8: 80percent AcOH / 72 h / 40 °C

9: 75 percent / BF₃*Et₂O / CH₂Cl₂ / Ambient temperature

With pyridine; sodium chlorate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; acetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/0040-4039(92)88092-J

Reference yield:

: 143537-14-8
C₁₃H₁₈O₄

: 143537-21-7
Benzoic acid (1R,2R,3S,5S)-3,5-bis-acetoxymethyl-2-((R)-2,2-bis-ethylsulfanyl-1-hydroxy-ethyl)-1-hydroxy-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 73 percent / pyridine

2: 1) NaIO₄, OsO₄, 2) NaClO₃ / 1) EtOH, water, 2) 70percent EtOH, 45-50 deg C

3: 98 percent / NaIO₄ / aq. ethanol / Ambient temperature

4: 81 percent / NaBH₄ / methanol

5: 88 percent / pyridine

6: 80percent AcOH / 72 h / 40 °C

7: 75 percent / BF₃*Et₂O / CH₂Cl₂ / Ambient temperature

With pyridine; sodium chlorate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; boron trifluoride diethyl etherate; acetic acid; In methanol; ethanol; dichloromethane;
DOI:10.1016/0040-4039(92)88092-J