5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose

Base Information

• Chemical Name: 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose
• CAS No.: 220542-32-5
• Molecular Formula: C₄₆H₅₅NO₉
• Molecular Weight: 765.944
• Mol file: 220542-32-5.mol

Synonyms:5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose

Chemical Property of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose

There total 1 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose 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: 20.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) + (4R)-2,2-dimethyl-N-(tert-butoxycarbonyl)-4-(1-trimethylsilyloxyvinyl)-1,3-oxazolidine (213819-91-1) → (4R)-4-acetyl-2,2-dimethyl-N-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)oxycarbonyl]-1,3-oxazolidine + 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-3-deculose (220542-33-6) + 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose (220542-32-5) + 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)oxycarbonylamino]-D-erythro-L-gulo-3-deculose

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃; for 1.16667h; Further byproducts given;

DOI:10.1021/jo981861h

Reference yield: 43.0%

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose (220542-32-5) → 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto/D-erythro-L-talo-3-deculose

Guidance literature:

With 4 A molecular sieve; tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; for 4.1h;

DOI:10.1021/jo981861h

Reference yield:

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose (220542-32-5) → (R)-4-[1-Hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:

With sodium tetrahydroborate; In methanol; diethyl ether; at -20 ℃; for 1h;

DOI:10.1021/jo981861h

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

(4R)-2,2-dimethyl-N-(tert-butoxycarbonyl)-4-(1-trimethylsilyloxyvinyl)-1,3-oxazolidine

Downstream raw materials:

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-deconic acid

methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate