Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester

Base Information

• Chemical Name: Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester
• CAS No.: 84786-84-5
• Molecular Formula: C₄₁H₅₀O₆S₂Si
• Molecular Weight: 731.062

Synonyms:Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester

Chemical Property of Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester

There total 12 articles about Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester 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:

benzoyl chloride (98-88-4) + (7S,8R,9S)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]nonan-7-ol (84786-83-4) → Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester (84786-84-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 23 ℃;

DOI:10.1021/ja00344a047

Reference yield:

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) → Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester (84786-84-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: K₂CO₃ / methanol / 1.5 h / 23 °C

3: 90 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

4: zinc triflate / CH₂Cl₂ / 5 h / 23 °C

5: diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

6: 90 percent / 1.) dimsyl sodium / 2.) DMSO, 25 deg C, 4 h

7: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 23 °C

With dichloro-acetic acid; dmap; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium methylsulfinylmethanide; potassium carbonate; triethylamine; diisopropyl-carbodiimide; In methanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1021/ja00344a047

Reference yield:

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) → Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester (84786-84-5)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 3 h / 40 °C

2: NaI / dimethylformamide / 3 h / 100 °C

3: K₂CO₃ / acetonitrile / 24 h / Heating

4: 90 percent / 1.) dimsyl sodium / 2.) DMSO, 25 deg C, 4 h

5: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 23 °C

With dmap; sodium methylsulfinylmethanide; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00344a047

upstream raw materials:

benzoyl chloride

(7S,8R,9S)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]nonan-7-ol

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

(3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one

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