methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate

Base Information

• Chemical Name: methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate
• CAS No.: 74055-36-0
• Molecular Formula: C₂₁H₄₂O₄Si₂
• Molecular Weight: 414.733
• Mol file: 74055-36-0.mol

Synonyms:methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate

Chemical Property of methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate

There total 11 articles about methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-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:

methanol (67-56-1) + (3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde (74064-30-5) → methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate (74055-36-0)

Guidance literature:

With manganese(IV) oxide; sodium cyanide; In acetic acid; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(00)94991-8

Reference yield:

methyl shikimate (40983-58-2) → methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate (74055-36-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / Et₃N, DMAP / dimethylformamide / 4 h / 0 °C

2: 75 percent / DMAP / acetonitrile / 6 h / 20 °C

3: 1.) Et₂O, 20 deg C, 12h, 2.) 125 deg C, DMSO, 4h

4: 90 percent / DIBA-H / toluene / 2 h / -78 - -30 °C

5: nBu₃SnH, AIBN / toluene / 3 h / 100 °C

6: MnO₂ / hexane / 12 h / 20 °C

7: MnO₂, NaCN / acetic acid / 12 h / 20 °C

With dmap; manganese(IV) oxide; 2,2'-azobis(isobutyronitrile); sodium cyanide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; In hexane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)94991-8

Reference yield:

(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether (74055-37-1) → methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate (74055-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: MnO₂ / hexane / 12 h / 20 °C

2: MnO₂, NaCN / acetic acid / 12 h / 20 °C

With manganese(IV) oxide; sodium cyanide; In hexane; acetic acid;

DOI:10.1016/S0040-4039(00)94991-8

upstream raw materials:

methanol

(3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde

methyl (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-ene-1-carboxylate

tert-butyldimethylsilyl chloride

Downstream raw materials:

1-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-2-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-2-(toluene-4-sulfonyl)-ethanone

(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

1α-hydroxyvitamin D3

(3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde