methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate
CAS No.:623163-88-2
Molecular Formula:C₂₀H₄₀O₆Si₂
Molecular Weight:432.705
Hs Code.:

Synonyms:methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

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Chemical Property of methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

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Technology Process of methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

There total 3 articles about methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate 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: 56.0%

: 439290-17-2
methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate

: 623163-88-2
methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: With lithium hydroxide; sulfamic acid methyl ester; 4-methylmorpholine N-oxide; potassium osmate(VI); In acetone; tert-butyl alcohol; at 20 ℃; for 16h;
DOI:10.1002/chem.200204265

Reference yield:

: 176487-06-2
(2S,3S)-(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid

: 623163-88-2
methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / HCl / 48 h / 20 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 18 h / 20 °C

3: 56 percent / MeSO₃NH₂; aq. LiOH; N-methylmorpholine N-oxide / K₂OsO₄ / acetone; 2-methyl-propan-2-ol / 16 h / 20 °C

With hydrogenchloride; lithium hydroxide; sulfamic acid methyl ester; 4-methylmorpholine N-oxide; triethylamine; potassium osmate(VI); In dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1002/chem.200204265

Reference yield:

: 439213-14-6
(5S,6S)-methyl 5,6-dihydroxycyclohexa-1,3-dienecarboxylate

: 623163-88-2
methyl (3R,4R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-3,4-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 18 h / 20 °C

2: 56 percent / MeSO₃NH₂; aq. LiOH; N-methylmorpholine N-oxide / K₂OsO₄ / acetone; 2-methyl-propan-2-ol / 16 h / 20 °C

With lithium hydroxide; sulfamic acid methyl ester; 4-methylmorpholine N-oxide; triethylamine; potassium osmate(VI); In dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1002/chem.200204265