(3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one

Base Information

• Chemical Name: (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one
• CAS No.: 581060-31-3
• Molecular Formula: C₂₅H₃₉N₃O₆Si
• Molecular Weight: 505.687

Synonyms:(3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one

Chemical Property of (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one

There total 19 articles about (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-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: 86.0%

(3S,4R,4aS,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-4-(p-toluenesulfonyloxy)-perhydroisochroman-1-one (581060-44-8) → (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one (581060-31-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 110 ℃;

DOI:10.1016/S0040-4039(03)01186-9

Reference yield:

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one (581060-31-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 40 percent / diethyl ether / 2 h / -78 °C

2.1: 87 percent / acetic acid; LiBH₄ / tetrahydrofuran / 0.17 h / 0 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

4.1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

5.1: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

6.1: ozone / methanol / 0.1 h / -78 °C

6.2: 80 percent / Me₂S / methanol / 3 h / -78 - 20 °C

7.1: 83 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 0 - 20 °C

8.1: 86 percent / NaN₃ / dimethylformamide / 4 h / 110 °C

With dipyridinium dichromate; lithium borohydride; n-butyllithium; sodium azide; 4 A molecular sieve; copper(l) cyanide; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-methoxymethoxy-2-[(R)-2-oxo-1-(toluene-4-sulfonyloxy)-propyl]-cyclohexanecarboxylic acid (581060-42-6) → (3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one (581060-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: 216 mg / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 86 percent / NaN₃ / dimethylformamide / 4 h / 110 °C

With dmap; sodium tetrahydroborate; sodium azide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.04.079

upstream raw materials:

(3S,4R,4aS,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-4-(p-toluenesulfonyloxy)-perhydroisochroman-1-one

(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

(2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Downstream raw materials:

(3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one

(3S,4S,5S,6S,10S)-4-azido-6-benzyloxy-5,8-dihydroxy-3-methyl-5,6,7,4a-tetrahydroisochroman-1-one

N-benzyloxycarbonyl-(-)-actinobolin

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