Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester
• CAS No.: 173044-09-2
• Molecular Formula: C₄₁H₇₆O₆Si₂
• Molecular Weight: 721.222

Synonyms:

Chemical Property of Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester

There total 13 articles about Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl 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:

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol (152934-39-9) → Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester (173044-09-2)

Guidance literature:

Multi-step reaction with 12 steps

2: 1.) t-BuLi / 1.) ether, -78 deg C

3: Swern oxidation

4: diethyl ether / -78 to -20 deg C

5: DDQ / CH₂Cl₂; H₂O / Ambient temperature

6: LiAlH₄ / diethyl ether / 0 °C

7: pyridine / 0 °C

8: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

9: K₂CO₃ / methanol / Ambient temperature

10: CSA / CH₂Cl₂ / 0 °C

11: imidazole / CH₂Cl₂ / 0 deg C to room temp.

12: TEA, DMAP / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane (144534-92-9) → Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester (173044-09-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) t-BuLi / 1.) ether, -78 deg C

2: Swern oxidation

3: diethyl ether / -78 to -20 deg C

4: DDQ / CH₂Cl₂; H₂O / Ambient temperature

5: LiAlH₄ / diethyl ether / 0 °C

6: pyridine / 0 °C

7: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

8: K₂CO₃ / methanol / Ambient temperature

9: CSA / CH₂Cl₂ / 0 °C

10: imidazole / CH₂Cl₂ / 0 deg C to room temp.

11: TEA, DMAP / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(2S,3R,5R,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-2-(4-methoxy-benzyloxy)-3-methyl-octanal (144534-80-5) → Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptyl ester (173044-09-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) t-BuLi / 1.) ether, -78 deg C

2: Swern oxidation

3: diethyl ether / -78 to -20 deg C

4: DDQ / CH₂Cl₂; H₂O / Ambient temperature

5: LiAlH₄ / diethyl ether / 0 °C

6: pyridine / 0 °C

7: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

8: K₂CO₃ / methanol / Ambient temperature

9: CSA / CH₂Cl₂ / 0 °C

10: imidazole / CH₂Cl₂ / 0 deg C to room temp.

11: TEA, DMAP / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61140-1

upstream raw materials:

acetic anhydride

(1R,2R,4R,5S)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-{(2S,4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-2,4-dimethyl-tetrahydro-furan-2-yl}-4-ethyl-2-methyl-heptan-1-ol

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol

Downstream raw materials:

Acetic acid (1R,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-hydroxymethyl-propyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptyl ester

Lysocellin

(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

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