4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

Base Information

Chemical Name:4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid
CAS No.:161984-60-7
Molecular Formula:C₃₁H₄₂O₇
Molecular Weight:526.67
Hs Code.:

Synonyms:4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

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Chemical Property of 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

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Technology Process of 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

There total 7 articles about 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid 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: 91.0%

: 161984-59-4
4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

: 161984-60-7
4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 65 ℃; for 8h;
DOI:10.1021/ja00108a051 DOI:10.1021/ja00146a009

Reference yield:

: 131311-17-6
[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

: 161984-60-7
4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 10 min, 2.) THF, 0 deg C, 0.5 h

2: 100 percent / H₂, Na₂CO₃ / 10percent Pd/C / ethyl acetate / 12 h / 25 °C

3: 97 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CHCl₂, from -78 to 0 deg C

5: NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 25 °C

6: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00146a009

Reference yield:

: 161984-56-1
(2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran

: 161984-60-7
4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / H₂, Na₂CO₃ / 10percent Pd/C / ethyl acetate / 12 h / 25 °C

2: 97 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CHCl₂, from -78 to 0 deg C

4: NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 25 °C

5: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00146a009