tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane
• CAS No.: 236390-91-3
• Molecular Formula: C₂₅H₄₄O₆Si
• Molecular Weight: 468.706
• Mol file: 236390-91-3.mol

Synonyms:

Chemical Property of tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane

There total 4 articles about tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane 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:

(2R,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-yn-3-ol (236390-86-6) → tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane (236390-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Lindlar catalyst

2: 75 percent / BuLi / -78 °C

3: 94 percent / IBr

4: K₂CO₃

5: 99 percent / i-Pr₂NEt, Bu₄BI

With n-butyllithium; hydrogen; iodine(I) bromide; potassium carbonate; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst;

DOI:10.1021/jo9902143

Reference yield:

(Z)-(2R,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol (236390-87-7) → tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane (236390-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / BuLi / -78 °C

2: 94 percent / IBr

3: K₂CO₃

4: 99 percent / i-Pr₂NEt, Bu₄BI

With n-butyllithium; iodine(I) bromide; potassium carbonate; N-ethyl-N,N-diisopropylamine;

DOI:10.1021/jo9902143

Reference yield:

Carbonic acid tert-butyl ester (Z)-(1R,2S)-1-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-(4-methoxy-benzyloxy)-2-methyl-pent-3-enyl ester (1026364-57-7) → tert-Butyl-{(2R,3S,4R)-4-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-2-methyl-pentyloxy}-dimethyl-silane (236390-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / IBr

2: K₂CO₃

3: 99 percent / i-Pr₂NEt, Bu₄BI

With iodine(I) bromide; potassium carbonate; N-ethyl-N,N-diisopropylamine;

DOI:10.1021/jo9902143

upstream raw materials:

(Z)-(2R,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol

(2R,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-yn-3-ol

Carbonic acid tert-butyl ester (Z)-(1R,2S)-1-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-(4-methoxy-benzyloxy)-2-methyl-pent-3-enyl ester

(4S,5R,6R)-4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-[(R)-1-iodo-2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-[1,3]dioxan-2-one