(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 196412-36-9
• Molecular Formula: C₄₁H₄₁NO₈
• Molecular Weight: 675.778

Synonyms:(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

Chemical Property of (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

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Technology Process of (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

There total 1 articles about (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl 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: 95.0%

dimethyl acetylenedicarboxylate (762-42-5) + ((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-oxo-piperidin-1-yl)-acetic acid (196412-35-8) → (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester (196412-36-9)

Guidance literature:

With acetic anhydride; In benzene; 2h, 25 deg C; 30 min, 90 deg C;

DOI:10.1002/hlca.19970800509

Reference yield: 78.0%

(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester (196412-36-9) → (5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester (204919-98-2) + (5R,6R,7R,8R)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester (204920-00-3)

Guidance literature:

With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane; at -7 ℃; for 3.5h; Yields of byproduct given;

DOI:10.1002/hlca.19980810303

Reference yield: 56.0%

(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester (196412-36-9) → ((5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-hydroxymethyl-5,6,7,8-tetrahydro-indolizin-1-yl)-methanol

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 7h;

DOI:10.1002/hlca.19970800509

upstream raw materials:

dimethyl acetylenedicarboxylate

((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-oxo-piperidin-1-yl)-acetic acid

Downstream raw materials:

(5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

(5R,6R,7R,8R)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

(5R,6R,7R,8S)-8-Amino-6,7-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

(5R,6R,7R,8S)-6,7-Bis-benzyloxy-5-benzyloxymethyl-8-(2,2,2-trifluoro-acetylamino)-5,6,7,8-tetrahydro-indolizine-1,2-dicarboxylic acid dimethyl ester

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