{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester
CAS No.:196094-20-9
Molecular Formula:C₃₄H₅₃NO₆Si
Molecular Weight:599.883
Hs Code.:

Synonyms:{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

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Chemical Property of {(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

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Technology Process of {(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

There total 11 articles about {(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl 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:

: (3S,4R,5R)-3,4-Bis-benzyloxy-5-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 196094-20-9
{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -18 ℃; Yield given;
DOI:10.1055/s-1997-962

Reference yield:

: 196094-12-9
(3S,4R,5R)-5-(3-Benzyloxy-propyl)-1-(4-methoxy-benzyl)-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one

: 196094-20-9
{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / HCOOH / Pd(black) / methanol

2: 97 percent / p-TsOH / methanol; CH₂Cl₂

3: Bu₄NF / CH₂Cl₂

4: 99 percent / Ag₂O / ethyl acetate

5: p-TsOH, MeOH

6: 81 percent / CAN / H₂O; acetonitrile

7: 72 percent / imidazole, DMAP / dimethylformamide

8: Et₃N, DMAP / CH₂Cl₂

9: tetrahydrofuran / -78 °C

10: NaBH₄, CeCl₃ / methanol / -18 °C

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; formic acid; cerium(III) chloride; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; palladium; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1055/s-1997-962

Reference yield:

: (3S,4S)-5-(3-Benzyloxy-propyl)-5-hydroxy-1-(4-methoxy-benzyl)-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one

: 196094-20-9
{(1R,2R,3R,4S)-2,3-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / -78 °C

2: 88 percent / HCOOH / Pd(black) / methanol

3: 97 percent / p-TsOH / methanol; CH₂Cl₂

4: Bu₄NF / CH₂Cl₂

5: 99 percent / Ag₂O / ethyl acetate

6: p-TsOH, MeOH

7: 81 percent / CAN / H₂O; acetonitrile

8: 72 percent / imidazole, DMAP / dimethylformamide

9: Et₃N, DMAP / CH₂Cl₂

10: tetrahydrofuran / -78 °C

11: NaBH₄, CeCl₃ / methanol / -18 °C

With 1H-imidazole; methanol; triethylsilane; dmap; sodium tetrahydroborate; formic acid; cerium(III) chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; palladium; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1055/s-1997-962