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

Base Information

• Chemical Name: (3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one
• CAS No.: 905312-38-1
• Molecular Formula: C₁₉H₂₅N₃O₆
• Molecular Weight: 391.424

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one

There total 20 articles about (3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-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:

(3S,4S,5S,6S,8R,9R,10S)-4-azido-6-benzyloxy-8-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-3-methyl-perhydroisochroman-1-one (581060-31-3) → (3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one (905312-38-1)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile;

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,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one (905312-38-1)

Guidance literature:

Multi-step reaction with 9 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

9.1: HF; pyridine / acetonitrile / 0.17 h / 0 °C

With pyridine; dipyridinium dichromate; lithium borohydride; n-butyllithium; sodium azide; 4 A molecular sieve; hydrogen fluoride; 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:

(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one (581060-36-8) → (3S,4S,4aS,5S,6S,8R,8aR)-4-Azido-6-benzyloxy-8-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-1-one (905312-38-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

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

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 40 percent / diethyl ether / 2 h / -78 °C

3.1: 87 percent / acetic acid; LiBH₄ / tetrahydrofuran / 0.17 h / 0 °C

4.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

5.1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

6.1: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

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

7.2: 80 percent / Me₂S / methanol / 3 h / -78 - 20 °C

8.1: 83 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 0 - 20 °C

9.1: 86 percent / NaN₃ / dimethylformamide / 4 h / 110 °C

10.1: HF; pyridine / acetonitrile / 0.17 h / 0 °C

With pyridine; dipyridinium dichromate; lithium borohydride; n-butyllithium; sodium azide; 4 A molecular sieve; hydrogen fluoride; copper(l) cyanide; ozone; acetic acid; methanesulfonyl chloride; triethylamine; 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

upstream raw materials:

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

N-benzyloxycarbonyl-(-)-actinobolin

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

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