(2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester

Base Information

• Chemical Name: (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester
• CAS No.: 896448-10-5
• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.364
• Mol file: 896448-10-5.mol

Synonyms:

Chemical Property of (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester

There total 1 articles about (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl 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%

methanol (67-56-1) + (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione (97506-01-9) → (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester (896448-10-5)

Guidance literature:

for 15h;

DOI:10.1002/hlca.200690066

Reference yield:

(2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester (896448-10-5) → 6-diphenylmethyl 5-amino-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,5-lactam (853799-39-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (i-Pr)2NEt / tetrahydrofuran / 2 h / -15 - 0 °C

2.1: NaBH₄ / methanol / 3 h / 0 °C

3.1: 35 percent / trichloroisocyanuric acid; TEMPO / tetrahydrofuran / -70 - -10 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 80 percent / tetrahydrofuran / 1 h

5.1: 75 percent / (DHQ)2PHAL; K₃[Fe(CN)6]; K₂CO₃ / MeSO₂NH₂; OsO₄ / H₂O; 2-methyl-propan-2-ol / 6 h / 0 - 5 °C

6.1: 93 percent / CH₂Cl₂ / 0.08 h / -78 °C

7.1: 98 percent / tetramethylguanidinium azide / CH₂Cl₂ / 3 h / -90 - 10 °C

8.1: 65 percent / H₂ / Pd/CaCO₃ / ethanol / 4 h / 750.06 Torr

9.1: LiOH*H₂O / methanol; H₂O / 1 h / 0 °C

10.1: 113 mg / acetone / 4 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium tetrahydroborate; Hydroquinone 1,4-phthalazinediyl diether; trichloroisocyanuric acid; hydrogen; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; potassium hexacyanoferrate(III); Lindlar's catalyst; osmium(VIII) oxide; methanesulfonamide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; 4.1: Wittig-Horner olefination / 4.2: Wittig-Horner olefination;

DOI:10.1002/hlca.200690066

Reference yield:

(2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester (896448-10-5) → 6-diphenylmethyl 5-amino-2,3-di-O-benzyl-5-deoxy-D-galactarate-1,5-lactam (853799-56-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (i-Pr)2NEt / tetrahydrofuran / 2 h / -15 - 0 °C

2.1: NaBH₄ / methanol / 3 h / 0 °C

3.1: 35 percent / trichloroisocyanuric acid; TEMPO / tetrahydrofuran / -70 - -10 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 80 percent / tetrahydrofuran / 1 h

5.1: 87 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 36 h

6.1: 94 percent / CH₂Cl₂ / -78 °C

7.1: 98 percent / tetramethylguanidinium azide / CH₂Cl₂ / -90 - 10 °C

8.1: 63 percent / H₂ / Pd/CaCO₃ / ethanol / 750.06 Torr

9.1: 12 percent / acetone

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; osmium(VIII) oxide; trichloroisocyanuric acid; hydrogen; sodium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; 4.1: Wittig-Horner olefination / 4.2: Wittig-Horner olefination;

DOI:10.1002/hlca.200690066

upstream raw materials:

methanol

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione

Downstream raw materials:

4-methyl 2,3-di-O-benzyl-L-threouronate

1,6-dimethyl (Z)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

6-ethyl 2,3-di-O-benzyl-L-idarate-1,4-lactone