(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

Base Information

Chemical Name:(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide
CAS No.:262615-01-0
Molecular Formula:C₄₁H₅₇NO₈Si
Molecular Weight:719.991
Hs Code.:

(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

Synonyms:(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

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Chemical Property of (2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

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Technology Process of (2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

There total 5 articles about (2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide 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: 95.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: (2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-1-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-2-methyl-butan-1-one

: 262615-01-0
(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

Guidance literature:: With trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane; at -5 ℃; for 1.83333h;
DOI:10.1021/ol0000049

Reference yield: 92.0%

: 262614-91-5
C₄₅H₆₁NO₇S₂Si

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 262615-01-0
(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.666667h;

C₄₅H₆₁NO₇S₂Si; In tetrahydrofuran; hexane; dichloromethane; at -15 - -5 ℃; for 1.75h;
DOI:10.1135/cccc2008181

Reference yield:

: ((2R,4S,6R,8R,10S)-8-Allyl-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-diphenyl-silane

: 262615-01-0
(2R,3S)-4-[(2R,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-butyramide

Guidance literature:: Multi-step reaction with 4 steps

1: OsO₄; NMO / H₂O; tetrahydrofuran / 0.83 h / 20 °C

2: NaIO₄ / H₂O; tetrahydrofuran / 1.5 h / 20 °C

3: 96 percent / Sn(OTf)2; N-ethylpiperidine / CH₂Cl₂ / 3.25 h / -78 °C

4: 95 percent / Me₃Al / hexane; CH₂Cl₂; tetrahydrofuran / 1.83 h / -5 °C

With 1-ethyl-piperidine; sodium periodate; osmium(VIII) oxide; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane; water; 1: dihydroxylation / 2: Oxidation / 3: Addition / 4: Substitution;
DOI:10.1021/ol0000049