methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate
• CAS No.: 208720-47-2
• Molecular Formula: C₉H₁₄O₇S
• Molecular Weight: 266.272

Synonyms:methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate

Chemical Property of methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate

Chemical Property:

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Technology Process of methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate

There total 8 articles about methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate 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: 95.0%

(3R,4S,5R)-methyl 5-methanesulfonyloxy-3,4-O-thionylshikimate (1422466-67-8) → methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate (208720-47-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/cjoc.201201000

Reference yield: 85.0%

(3aR,7R,7aR)-7-Methanesulfonyloxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester → methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate (208720-47-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1.5h; Reflux;

Reference yield:

C11H16O8S → methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate (208720-47-2)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 0.25h;

DOI:10.1021/acs.jmedchem.6b00483

upstream raw materials:

methyl shikimate

(3R,4S,5R)-methyl 3,4-O-thionylshikimate

(3R,4S,5R)-methyl 5-methanesulfonyloxy-3,4-O-thionylshikimate

Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate

Downstream raw materials:

(3R,4S,5R)-methyl 4-hydroxy-5-methanesulfonyloxy-3-tosyloxycyclohex-1-enecarboxylate

methyl (3R,4S,5R)-5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate

(3R,4R,5S)-4-Amino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

(3R,4R,5S)-4-Acetylamino-5-amino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

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