(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal

Base Information

• Chemical Name: (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal
• CAS No.: 869338-58-9
• Molecular Formula: C₄₁H₇₆O₇Si₂
• Molecular Weight: 737.221
• Mol file: 869338-58-9.mol

Synonyms:(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal

Chemical Property of (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal

There total 7 articles about (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal 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: 96.0%

(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptan-1-ol (869338-57-8) → (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal (869338-58-9)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1021/ol051691c

Reference yield:

(2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-3-methoxymethoxy-2-methyl-pentan-1-ol (869338-33-0) → (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal (869338-58-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -30 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

2.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

2.3: 61 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

3.1: 92 percent / DIBAL

4.1: 96 percent / Dess-Martin periodinane

With 2,6-dimethylpyridine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1021/ol051691c

Reference yield:

(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol (869338-49-8) → (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal (869338-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 71 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

2.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

3.1: 90 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -30 °C

5.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

5.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

5.3: 61 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

6.1: 92 percent / DIBAL

7.1: 96 percent / Dess-Martin periodinane

With 2,6-dimethylpyridine; water; tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; pentane;

DOI:10.1021/ol051691c

upstream raw materials:

(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptan-1-ol

(2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-3-methoxymethoxy-2-methyl-pentan-1-ol

(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol

(2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-1-(4-methoxy-benzyloxy)-2-methyl-pentan-3-ol

Downstream raw materials:

1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

(2S,3R,4S)-4-{(1S,2S)-2-[(Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-deca-7,9-dienyl]-cyclopropyl}-3-methoxymethoxy-2-methyl-pentan-1-ol

C₆₀H₁₀₈O₉Si₃