(R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one

Base Information

• Chemical Name: (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one
• CAS No.: 1063694-11-0
• Molecular Formula: C₄₀H₇₄O₇Si₃
• Molecular Weight: 751.28
• Mol file: 1063694-11-0.mol

Synonyms:(R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one

Chemical Property of (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one

There total 2 articles about (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one 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:

5-[(benzyloxy)methyl]hex-5-en-2-one (1063693-74-2) + (2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde (1063693-69-5) → (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one (1063694-11-0)

Guidance literature:

5-[(benzyloxy)methyl]hex-5-en-2-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.0666667h; Inert atmosphere;

(2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; diastereoselective reaction; Inert atmosphere; Saturated solution;

DOI:10.1021/ol8015868

Reference yield:

C17H26O2Si (1063694-17-6) + (2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde (1063693-69-5) → (R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one (1063694-11-0)

Guidance literature:

With boron trifluoride diethyl etherate; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol8015868

Reference yield: 91.0%

(R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one (1063694-11-0) + methyllithium (917-54-4) → (1R,3R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol + (1R,3S)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol (1063693-65-1)

Guidance literature:

methyllithium; With titanium(IV) isopropylate; titanium tetrachloride; In diethyl ether; at 0 ℃; Inert atmosphere;

(R)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-1-hydroxy-hept-6-en-3-one; In diethyl ether; at -78 - 0 ℃; for 0.333333h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol8015868

upstream raw materials:

5-[(benzyloxy)methyl]hex-5-en-2-one

(2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde

C₁₇H₂₆O₂Si

Downstream raw materials:

(1R,3S)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol