(2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester

Base Information

• Chemical Name: (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester
• CAS No.: 333788-77-5
• Molecular Formula: C₁₉H₂₈O₇
• Molecular Weight: 368.427
• Mol file: 333788-77-5.mol

Synonyms:(2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester

Chemical Property of (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester

There total 1 articles about (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester 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: 100.0%

2-Methoxypropene (116-11-0) + (2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate (119770-87-5,104211-01-0) → (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester (333788-77-5)

Guidance literature:

With trichlorophosphate; In dichloromethane;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield: 91.0%

(2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester (333788-77-5) → (2S,3S)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-butane-1,4-diol (333788-78-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

(2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester (333788-77-5) → (R)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-2-(4-methoxy-benzyloxy)-ethanol (333788-67-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 91 percent / LiAlH₄ / tetrahydrofuran / 0 °C

2: 86 percent / PPTS / 1,2-dichloro-ethane / 60 °C

3: 100 percent / TEA; DMAP / CH₂Cl₂

4: 93 percent / diethyl ether / -65 - 0 °C

5: 97 percent / PPTS / ethanol / 80 °C

6: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

7: 98 percent / TEA; DMAP / CH₂Cl₂

8: 96 percent / TBAF / tetrahydrofuran

9: 93 percent / EDA / dimethylsulfoxide / 0 °C

10: 98 percent / AgNO₃; pyridine / acetonitrile

11: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

12: 99 percent / H₂; quinoline / Lindlar cat. / methanol

13: 98 percent / TEA; DMAP / CH₂Cl₂

14: 91 percent / TBAF / tetrahydrofuran / 50 °C

15: 75 percent / (Bu₃Sn)2O; Zn(OTf)2O / toluene / Heating

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; lithium aluminium tetrahydride; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; silver nitrate; bis(tri-n-butyltin)oxide; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene; acetonitrile; 11: Yamaguchi coupling reaction;

DOI:10.1016/S0040-4039(00)02281-4

upstream raw materials:

2-Methoxypropene

(2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate

Downstream raw materials:

(2S,3S)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-butane-1,4-diol

2-O-benzyl-3,4-O-isopropylidene-L-threitol

(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

(R)-2-((S)-1-(benzyloxy)propyl)oxirane

Refernces