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

Base Information

• Chemical Name: (1S,2R,3R)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate
• CAS No.: 339570-94-4
• Molecular Formula: C₃₁H₄₁N₃O₇
• Molecular Weight: 567.682
• Mol file: 339570-94-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (1S,2R,3R)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate 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:

(2R,3S,4S)-4-(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-2,5-dimethyl-3-hexanol (126587-67-5) → (1S,2R,3R)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate (339570-94-4)

Guidance literature:

Multi-step reaction with 9 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

6: 94 percent / Amberlyst 15 / methanol / 20 h

7: Dess-Martin reagent / CH₂Cl₂ / 4 h

8: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

9: 94.1 mg / DMAP; DCC / CH₂Cl₂

With dmap; sodium chlorite; lithium aluminium tetrahydride; formic acid; Amberlyst 15; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 7: Dess-Martin oxidation;

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)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate (339570-94-4)

Guidance literature:

Multi-step reaction with 8 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

5: 94 percent / Amberlyst 15 / methanol / 20 h

6: Dess-Martin reagent / CH₂Cl₂ / 4 h

7: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

8: 94.1 mg / DMAP; DCC / CH₂Cl₂

With dmap; sodium chlorite; lithium aluminium tetrahydride; formic acid; Amberlyst 15; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 6: Dess-Martin oxidation;

DOI:10.1021/jo001640n

Reference yield:

(2R,3R,4S)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2,5-dimethyl-3-hexanol (339570-89-7) → (1S,2R,3R)-1-isopropyl-2-(methoxymethoxy)-3-methylbutanoic benzyl ester, ester with (1S,2S,3S)-3-azido-2-benzyloxycyclohexanecarboxylate (339570-94-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / DIEA / CH₂Cl₂ / 20 °C

2: 89 percent / HCO₂H / Pd / methanol / 0.33 h

3: 47 percent / DMAP; DCC / toluene

4: 94 percent / Amberlyst 15 / methanol / 20 h

5: Dess-Martin reagent / CH₂Cl₂ / 4 h

6: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

7: 94.1 mg / DMAP; DCC / CH₂Cl₂

With dmap; sodium chlorite; formic acid; Amberlyst 15; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In methanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 5: Dess-Martin oxidation;

DOI:10.1021/jo001640n

upstream raw materials:

benzyl alcohol

(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

(1R,5S,8S)-8-hydroxy-7-oxa-bicyclo[3.2.1]-octan-6-one

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