(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

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Chemical Name:(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one
CAS No.:189348-04-7
Molecular Formula:C₄₆H₅₆O₈Si
Molecular Weight:765.031
Hs Code.:

(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

Synonyms:(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

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Chemical Property of (2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

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Technology Process of (2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

There total 19 articles about (2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one 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: 76.0%

: 189348-02-5
(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

: 189348-04-7
(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

Guidance literature:: With boron trifluoride diethyl etherate; In chloroform; at 0 ℃;
DOI:10.1021/ja9701523

Reference yield:

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 189348-04-7
(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 92 percent / PPTS / CH₂Cl₂; methanol / 2 h / -20 °C

3: 96 percent / Et₃N, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 3 h / Ambient temperature

4: 63 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

5: 76 percent / BF₃*OEt₂ / CHCl₃ / 1 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1021/jo980320p

Reference yield:

: 189347-91-9
benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether

: 189348-04-7
(2R,4S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-4a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min

2: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

3: 90 percent / p-TsOH*H₂O / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

4: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

5: 98 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 92 percent / PPTS / CH₂Cl₂; methanol / 2 h / -20 °C

8: 96 percent / Et₃N, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 3 h / Ambient temperature

9: 63 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

10: 76 percent / BF₃*OEt₂ / CHCl₃ / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1021/jo980320p