(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

Base Information

Chemical Name:(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester
CAS No.:849372-35-6
Molecular Formula:C₂₇H₄₃NO₇Si
Molecular Weight:521.726
Hs Code.:

(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

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Chemical Property of (3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

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Technology Process of (3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

There total 10 articles about (3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl 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:

: (3aS,6R,6aS)-6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 849372-35-6
(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / n-BuLi / tetrahydrofuran

2: 78 percent / PCC; 4 Angstroem MS / CH₂Cl₂

3: NaBH(OAc)3; 4 Angstroem MS; AcOH / CH₂Cl₂ / 40 °C

4: KHCO₃ / ethyl acetate; H₂O

5: 97 percent / Grubbs' catalyst / CH₂Cl₂ / 24 h / 45 °C

6: 96 percent / OsO₄; NMO / acetone; H₂O

7: CSA / acetone

With osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; N-methyl-2-indolinone; 4 Angstroem MS; camphor-10-sulfonic acid; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 1: Wittig reaction;
DOI:10.3987/COM-04-S(P)45

Reference yield:

: 849372-21-0
(4R,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethan-1-one

: 849372-35-6
(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH(OAc)3; 4 Angstroem MS; AcOH / CH₂Cl₂ / 40 °C

2: KHCO₃ / ethyl acetate; H₂O

3: 97 percent / Grubbs' catalyst / CH₂Cl₂ / 24 h / 45 °C

4: 96 percent / OsO₄; NMO / acetone; H₂O

5: CSA / acetone

With osmium(VIII) oxide; Grubbs catalyst first generation; N-methyl-2-indolinone; 4 Angstroem MS; camphor-10-sulfonic acid; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; acetic acid; In dichloromethane; water; ethyl acetate; acetone;
DOI:10.3987/COM-04-S(P)45

Reference yield:

: 849372-15-2
5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-lyxono-1,4-lactone

: 849372-35-6
(3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / DIBAL-H / toluene / -40 °C

2: 77 percent / n-BuLi / tetrahydrofuran

3: 78 percent / PCC; 4 Angstroem MS / CH₂Cl₂

4: NaBH(OAc)3; 4 Angstroem MS; AcOH / CH₂Cl₂ / 40 °C

5: KHCO₃ / ethyl acetate; H₂O

6: 97 percent / Grubbs' catalyst / CH₂Cl₂ / 24 h / 45 °C

7: 96 percent / OsO₄; NMO / acetone; H₂O

8: CSA / acetone

With osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; N-methyl-2-indolinone; 4 Angstroem MS; camphor-10-sulfonic acid; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; potassium hydrogencarbonate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; toluene; 2: Wittig reaction;
DOI:10.3987/COM-04-S(P)45