(1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate

Base Information

• Chemical Name: (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate
• CAS No.: 339570-92-2
• Molecular Formula: C₃₀H₅₁N₃O₆Si
• Molecular Weight: 577.837
• Mol file: 339570-92-2.mol

Synonyms:(1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate

Chemical Property of (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate

There total 14 articles about (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate 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: 47.0%

(1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylic acid (197505-19-4) + (3S,4R,5R)-6-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol (339570-91-1) → (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate (339570-92-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene;

DOI:10.1021/jo001640n

Reference yield:

(2R,3S,4S)-4-(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-2,5-dimethyl-3-hexanol (126587-67-5) → (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate (339570-92-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

2: 44 percent / LiAlH₄ / diethyl ether / 2 h / -10 °C

3: 98 percent / DIEA / CH₂Cl₂ / 20 °C

4: 89 percent / HCO₂H / Pd / methanol / 0.33 h

5: 47 percent / DMAP; DCC / toluene

With dmap; lithium aluminium tetrahydride; formic acid; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo001640n

Reference yield:

(2R,4S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,5-dimethyl-hexan-3-one (339570-88-6) → (1S,2R,3R)-4-[(tert-butyldimethylsilyl)oxy]-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S,3S)-3-azido-2-benzyloxy-cyclohexanecarboxylate (339570-92-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / LiAlH₄ / diethyl ether / 2 h / -10 °C

2: 98 percent / DIEA / CH₂Cl₂ / 20 °C

3: 89 percent / HCO₂H / Pd / methanol / 0.33 h

4: 47 percent / DMAP; DCC / toluene

With dmap; lithium aluminium tetrahydride; formic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo001640n

upstream raw materials:

(1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylic acid

(3S,4R,5R)-6-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol

(2R,3S,4S)-4-(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-2,5-dimethyl-3-hexanol

acetic acid (6S)-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-(1R)-cyclohex-2-enyl ester

Downstream raw materials:

C₇₀H₉₅N₅O₁₇

cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl]

(1S,2R,3R)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate

(1S,2S,3S)-3-Amino-2-benzyloxy-cyclohexanecarboxylic acid (1S,2R,3S)-3-benzyloxycarbonyl-1-isopropyl-2-methoxymethoxy-butyl ester