(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

Base Information

Chemical Name:(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran
CAS No.:169888-23-7
Molecular Formula:C₃₇H₄₀O₆
Molecular Weight:580.721
Hs Code.:

Synonyms:(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

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Chemical Property of (1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

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Technology Process of (1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

There total 4 articles about (1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran 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: 53.0%

: 4,8-anhydro-5,6,7,9-tetra-O-benzyl-2,3-dideoxy-D-gluco-non-3-enitol

: 169888-23-7
(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

: (5S,7R,8R,9S,10R)-8,9,10-tris-benzyloxy-7-benzyloxymethyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 5h;
DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield: 17.0%

: 139195-44-1
2,3,4,6-tetra-O-benzyl-1-deoxy-1-(3'-hydroxypropyl)-α-D-glucopyranose

: 169888-23-7
(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

: (5S,7R,8R,9S,10R)-8,9,10-tris-benzyloxy-7-benzyloxymethyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:: With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; at 40 ℃; for 1h; Irradiation;
DOI:10.1016/0040-4039(95)00766-6

Reference yield:

: 82659-52-7
1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

: 169888-23-7
(1R)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranosyl-1-spiro-2'-tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) BH₃*THF, 2.) aq. NaOH, aq.H₂O₂ / 1.) THF, room temperature, 5 h, 2.) <40 deg C, 0.5 h

2: 51 percent / (diacetoxyiodo)benzene, I₂ / cyclohexane / 1 h / 40 °C / Irradiation

With sodium hydroxide; borane-THF; [bis(acetoxy)iodo]benzene; dihydrogen peroxide; iodine; In cyclohexane;
DOI:10.1021/jo960060g