(2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol

Base Information

• Chemical Name: (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol
• CAS No.: 609355-86-4
• Molecular Formula: C₃₃H₄₉N₃O₄S₂
• Molecular Weight: 615.902

Synonyms:(2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol

Chemical Property of (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol

There total 21 articles about (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol 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: 87.0%

(2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-3-methoxymethoxy-6-methyl-octan-2-ol (609355-67-1) → (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol (609355-86-4)

Guidance literature:

With dimethylsulfide; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(03)01553-3

Reference yield:

benzyl bromide (100-39-0) → (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol (609355-86-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: NaBO₃*4H₂O / dimethylformamide

2.3: NaH / dimethylformamide / 0 - 20 °C

3.1: 70 percent / p-TsOH / methanol; CH₂Cl₂ / 20 °C

4.1: IBX; DMSO / 20 °C

4.2: 90 percent / KOt-Bu / tetrahydrofuran / 0 °C

5.1: 83 percent / AD mix-β; CH3SO2NH2; OsO4 / 2-methyl-propan-2-ol; H2O / 20 °C

6.1: PhCH(OMe)2; CSA / CH₂Cl₂ / 20 °C

6.2: LiAlH₄ / tetrahydrofuran / 0 °C

6.3: 76 percent / p-TsOH / methanol / 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

8.1: K₂CO₃ / ethanol / 20 °C

9.1: 67 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

10.1: n-BuLi / tetrahydrofuran / 0.08 h / 20 °C

10.2: 92 percent / tetrahydrofuran / 0.33 h / 0 °C

11.1: 81 percent / TBAF / tetrahydrofuran / 20 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

13.1: NaN₃ / dimethylformamide / 50 °C

14.1: 87 percent / BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0 °C

With dmap; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; sodium azide; dimethylsulfide; methanesulfonamide; benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01553-3

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-6-methyl-octane-2,3-diol (609355-86-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: imidazole / CH₂Cl₂ / 20 °C

1.2: 86 percent / K₂CO₃ / methanol / 20 °C

2.1: 90 percent / IBX; DMSO / 20 °C

3.1: 96 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

4.1: 89 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: n-BuLi / tetrahydrofuran / 0.08 h / 20 °C

5.2: 92 percent / tetrahydrofuran / 0.33 h / 0 °C

6.1: 81 percent / TBAF / tetrahydrofuran / 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

8.1: NaN₃ / dimethylformamide / 50 °C

9.1: 87 percent / BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; n-butyllithium; sodium azide; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(03)01553-3

upstream raw materials:

(2R,3S,4R,6R)-1-[2-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-[1,3]dithian-2-yl]-4,8-bis-benzyloxy-3-methoxymethoxy-6-methyl-octan-2-ol

(2R,4S)-2,4-dimethylpentane-1,5-diol

benzyl bromide

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

Downstream raw materials:

(2S,3R)-5-((1S,3R)-4-Azido-1,3-dimethyl-butyl)-2-((1R,3R)-1,5-bis-benzyloxy-3-methyl-pentyl)-5-methoxy-tetrahydro-furan-3-ol

(2S,3R,5S,8R,10S)-2-((1R,3R)-1,5-Bis-benzyloxy-3-methyl-pentyl)-3-hydroxy-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

{(2R,4S)-4-[(4R,5S)-5-((1R,3R)-1,5-Bis-benzyloxy-3-methyl-pentyl)-4-hydroxy-2-methoxy-tetrahydro-furan-2-yl]-2-methyl-pentyl}-carbamic acid tert-butyl ester

{(2R,4S)-4-[(4R,5S)-5-((1R,3R)-1,5-Bis-benzyloxy-3-methyl-pentyl)-2,4-dihydroxy-tetrahydro-furan-2-yl]-2-methyl-pentyl}-carbamic acid tert-butyl ester

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