(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester
• CAS No.: 391658-39-2
• Molecular Formula: C₄₀H₄₄O₈
• Molecular Weight: 652.785
• Mol file: 391658-39-2.mol

Synonyms:(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester

Chemical Property of (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester

There total 1 articles about (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl 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: 61.0%

bromoacetic acid tert-butyl ester (5292-43-3) + 2,3,4,6-tetra-O-benzyl-D-galactonolactone (82598-84-3) → (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester (391658-39-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1021/ol0102343

Reference yield:

(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester (391658-39-2) → Hydroxy-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 12h;

DOI:10.1021/ol0102343

Reference yield:

(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester (391658-39-2) → (S)-Hydroxy-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Guidance literature:

With water; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ol0102343

upstream raw materials:

bromoacetic acid tert-butyl ester

2,3,4,6-tetra-O-benzyl-D-galactonolactone