(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

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Chemical Name:(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol
CAS No.:157220-22-9
Molecular Formula:C₃₄H₆₀O₉Si
Molecular Weight:640.931
Hs Code.:

(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

Synonyms:(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

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Chemical Property of (S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

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Technology Process of (S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

There total 8 articles about (S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol 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:

: 157220-15-0
(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

: 157220-22-9
(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, r.t., 2.) r.t.

3: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 °C

4: aq. AcOH / tetrahydrofuran / Ambient temperature

5: PDC, molecular sieves 4A / CH₂Cl₂ / Ambient temperature

6: 52 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

7: 79 percent / tetrahydrofuran / -78 °C

8: 1.) OsO₄, N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane, 2.) aq. NaHSO₃ / 1.) CH₂Cl₂, -90 deg C, 2.) THF, reflux

With 2,6-dimethylpyridine; sodium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; 4 A molecular sieve; dihydrogen peroxide; sodium hydrogensulfite; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00083a008

Reference yield:

: 157220-20-7
(4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

: 157220-22-9
(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 52 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

2: 79 percent / tetrahydrofuran / -78 °C

3: 1.) OsO₄, N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane, 2.) aq. NaHSO₃ / 1.) CH₂Cl₂, -90 deg C, 2.) THF, reflux

With osmium(VIII) oxide; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydrogensulfite; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/jo00083a008

Reference yield:

: (4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol

: 157220-22-9
(S)-3-((2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-2-hydroxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1: PDC, molecular sieves 4A / CH₂Cl₂ / Ambient temperature

2: 52 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

3: 79 percent / tetrahydrofuran / -78 °C

4: 1.) OsO₄, N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane, 2.) aq. NaHSO₃ / 1.) CH₂Cl₂, -90 deg C, 2.) THF, reflux

With osmium(VIII) oxide; dipyridinium dichromate; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; 4 A molecular sieve; sodium hydrogensulfite; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/jo00083a008