methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate

Base Information

• Chemical Name: methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate
• CAS No.: 439290-17-2
• Molecular Formula: C₂₀H₃₈O₄Si₂
• Molecular Weight: 398.69

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

Chemical Property of methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate

Chemical Property:

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Technology Process of methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate

There total 2 articles about methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate 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%

t-butyldimethylsiyl triflate (69739-34-0) + (5S,6S)-methyl 5,6-dihydroxycyclohexa-1,3-dienecarboxylate (439213-14-6) → methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate (439290-17-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/chem.200204265

Reference yield:

(2S,3S)-(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid (176487-06-2) → methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate (439290-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / HCl / 48 h / 20 °C

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

With hydrogenchloride; triethylamine; In dichloromethane;

DOI:10.1002/chem.200204265

Reference yield: 88.0%

methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate (439290-17-2) → [(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol (439213-17-9)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at 0 ℃; for 3h;

DOI:10.1039/b110420a

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

Downstream raw materials:

[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

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

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

benzoic acid 5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

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