(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

Base Information

Chemical Name:(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol
CAS No.:623163-89-3
Molecular Formula:C₁₉H₄₀O₅Si₂
Molecular Weight:404.695
Hs Code.:

Synonyms:(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

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Chemical Property of (1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

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Technology Process of (1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

There total 4 articles about (1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-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: 92.0%

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

: 623163-89-3
(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1002/chem.200204265

Reference yield:

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

: 623163-89-3
(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

Guidance literature:: Multi-step reaction with 4 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

4: 92 percent / DIBAL-H / CH₂Cl₂ / 3 h / 0 °C

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

Reference yield:

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

: 623163-89-3
(1R,2R,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethylcyclohex-3-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / MeSO₃NH₂; aq. LiOH; N-methylmorpholine N-oxide / K₂OsO₄ / acetone; 2-methyl-propan-2-ol / 16 h / 20 °C

2: 92 percent / DIBAL-H / CH₂Cl₂ / 3 h / 0 °C

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