(1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

Base Information

• Chemical Name: (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol
• CAS No.: 1229922-80-8
• Molecular Formula: C₁₇H₂₆ClNO₃
• Molecular Weight: 327.851

Synonyms:(1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

Chemical Property of (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

Chemical Property:

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Technology Process of (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

There total 2 articles about (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol 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: 40.0%

C18H29NO6S (1229922-83-1) + methanesulfonyl chloride (124-63-0) + triethylamine (121-44-8) → (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol (1229922-80-8) + (3aS,4R,5S,7aR)-4-acetamido-7-cyclohexyl-N,N,N-triethyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-ammonium methanesulfonate

Guidance literature:

C₁₈H₂₉NO₆S; methanesulfonyl chloride; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2010.03.059

Reference yield: 32.0%

(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol (1229922-77-3) → (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole (1229922-79-5) + (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol (1229922-80-8)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In 1,2-dichloro-ethane; at 4 - 60 ℃;

DOI:10.1016/j.tet.2010.03.059

Reference yield:

(1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol (1229922-80-8) → (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole (1229922-79-5)

Guidance literature:

With triethylamine; at 80 ℃;

DOI:10.1016/j.tet.2010.03.059

upstream raw materials:

(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol

C₁₈H₂₉NO₆S

methanesulfonyl chloride

triethylamine

Downstream raw materials:

(3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole

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