(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

Base Information

Chemical Name:(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
CAS No.:187038-09-1
Molecular Formula:C₂₉H₄₆O₅Si
Molecular Weight:502.767
Hs Code.:

(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

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Chemical Property of (1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

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Technology Process of (1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

There total 14 articles about (1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 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: 62.0%

: (2E,8E,10Z)-(4R,6S)-4-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-7-methoxymethoxy-2,6-dimethyl-dodeca-2,8,10-trienal

: 187038-09-1
(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

Guidance literature:: In toluene; for 72h; Heating; sealed tube;
DOI:10.1016/S0040-4039(96)02377-5

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 187038-09-1
(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / lutidine / CH₂Cl₂

2: NaOMe / methanol

3: PDC, zeolite / CH₂Cl₂

4: 62 percent / toluene / 72 h / Heating; sealed tube

With dipyridinium dichromate; zeolite; lutidine; sodium methylate; In methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4039(96)02377-5

Reference yield:

: 187038-02-4
(2R,4S)-2-Benzyloxy-5,5-bis-ethylsulfanyl-4-methyl-pentanal

: 187038-09-1
(1R,2R,4aR,5R,6S,8R,8aS)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1: 72 percent

2: CuO, CuCl₂ / acetone; H₂O

3: s-BuLi / diethyl ether / -100 °C

4: DIPEA / CH₂Cl₂

5: DIBAL / CH₂Cl₂

6: pyridine

7: TBAF / tetrahydrofuran

8: PCC, zeolite / CH₂Cl₂

9: 90 percent / lutidine / CH₂Cl₂

10: NaOMe / methanol

11: PDC, zeolite / CH₂Cl₂

12: 62 percent / toluene / 72 h / Heating; sealed tube

With pyridine; dipyridinium dichromate; zeolite; lutidine; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium methylate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; copper(II) oxide; copper dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene;
DOI:10.1016/S0040-4039(96)02377-5