Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Base Information

• Chemical Name: Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester
• CAS No.: 164215-45-6
• Molecular Formula: C₃₅H₅₂O₁₁Si
• Molecular Weight: 676.877

Synonyms:Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Chemical Property of Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

There total 18 articles about Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl 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: 90.0%

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-44-5) → Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-45-6)

Guidance literature:

With dichloro-acetic acid; In methanol;

DOI:10.1021/ja00102a074

Reference yield:

(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol (164215-29-6) → Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-45-6)

Guidance literature:

Multi-step reaction with 15 steps

1: Et₃N, DMAP

2: Et₃N / CH₂Cl₂

3: 1.) n-BuLi, LiBr / 1.) THF, 2.) THF

4: 93 percent / Dess-Martin oxidant

5: 60 percent / aq. Cr(OAc)2 / tetrahydrofuran / 65 °C

6: 93 percent / Bu₄NF / tetrahydrofuran

7: 1.) OsO₄, NMO, (DHQD)2PHAL, 2.) methanolic HCl, 3.) Et₃N, DMAP

8: 97 percent / DMAP / CH₂Cl₂ / 50 °C

9: 99 percent / H₂ / Pd(OH)2/C, Pd/CaCO₃

10: 90 percent / (COCl)2, DMSO / CH₂Cl₂

11: 78 percent / Me₃N / diethyl ether

12: 95 percent / AgNO₃, 2,6-lutidine

13: 84 percent / DIBAL-H / toluene

14: 95 percent / DMAP / CH₂Cl₂

15: 90 percent / Cl₂CHCO₂H / methanol

With 2,6-dimethylpyridine; hydrogenchloride; dichloro-acetic acid; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; chromium(II) acetate; Dess-Martin periodane; silver nitrate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; trimethylamine; palladium dihydroxide; Lindlar's catalyst; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00102a074

Reference yield:

(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-4-trimethylsilanyl-but-3-yne-1,2-diol (171189-78-9) → Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-45-6)

Guidance literature:

Multi-step reaction with 16 steps

1: methanolic K₂CO₃

2: Et₃N, DMAP

3: Et₃N / CH₂Cl₂

4: 1.) n-BuLi, LiBr / 1.) THF, 2.) THF

5: 93 percent / Dess-Martin oxidant

6: 60 percent / aq. Cr(OAc)2 / tetrahydrofuran / 65 °C

7: 93 percent / Bu₄NF / tetrahydrofuran

8: 1.) OsO₄, NMO, (DHQD)2PHAL, 2.) methanolic HCl, 3.) Et₃N, DMAP

9: 97 percent / DMAP / CH₂Cl₂ / 50 °C

10: 99 percent / H₂ / Pd(OH)2/C, Pd/CaCO₃

11: 90 percent / (COCl)2, DMSO / CH₂Cl₂

12: 78 percent / Me₃N / diethyl ether

13: 95 percent / AgNO₃, 2,6-lutidine

14: 84 percent / DIBAL-H / toluene

15: 95 percent / DMAP / CH₂Cl₂

16: 90 percent / Cl₂CHCO₂H / methanol

With 2,6-dimethylpyridine; hydrogenchloride; dichloro-acetic acid; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; chromium(II) acetate; potassium carbonate; Dess-Martin periodane; silver nitrate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; trimethylamine; palladium dihydroxide; Lindlar's catalyst; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00102a074

upstream raw materials:

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

2,2-Dimethyl-propionic acid (1S,3R,4S,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

Downstream raw materials:

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

(1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(2,2-dimethylpropionyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

(+)-zaragozic acid

(1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-4-hydroxy-5-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester

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