(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

Base Information

Chemical Name:(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane
CAS No.:121654-09-9
Molecular Formula:C₅₄H₅₆O₁₀
Molecular Weight:865.033
Hs Code.:

(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

Synonyms:(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

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Chemical Property of (1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

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Technology Process of (1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

There total 6 articles about (1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane 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%

: 121654-08-8
O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

: 121654-09-9
(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: With 3,3-dimethyldioxirane; In dichloromethane; at -55 ℃; for 12h; optical yield given as %de; stereoselective reaction;
DOI:10.1021/ol301349w

Reference yield:

: 121654-06-6
O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

: 121654-09-9
(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., 1 h

2: dimethyldioxirane / CH₂Cl₂ / 0.5 h / 0 °C

With 3,3-dimethyldioxirane; sodium hydride; In dichloromethane;
DOI:10.1021/ja00199a028

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 121654-09-9
(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 4 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

2: 56 percent / ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 1 h, 2.) -78 deg C -> r.t., 1 h; r.t., 18 h

3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., 1 h

4: dimethyldioxirane / CH₂Cl₂ / 0.5 h / 0 °C

With 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1021/ja00199a028