(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

Base Information

Chemical Name:(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
CAS No.:183954-70-3
Molecular Formula:C₅₆H₅₈O₁₂
Molecular Weight:923.069
Hs Code.:

(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

Synonyms:(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

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Chemical Property of (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

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Technology Process of (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

There total 6 articles about (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one 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:

: 78153-79-4,89025-46-7,94898-43-8,101966-50-1,122741-44-0,143615-35-4,94898-42-7
2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride

: 183954-70-3
(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 27 percent / AgClO₄, SnCl₂ / CH₂Cl₂; diethyl ether / 2.5 h / -20 °C

2: NaOMe, MeOH / CHCl₃ / 1.5 h / Ambient temperature

3: DL-camphorsulfonic acid / 1 h / Ambient temperature

4: NaH / 1.) DMF, RT, 17 h, 2.) DMF, from RT to 70 deg C, 2 h

5: 88 percent / 70percent aq. AcOH / 3 h / 60 °C

6: 1.) dibutyltin oxide, 2.) n-Bu₄NI / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 1 h

With methanol; camphor-10-sulfonic acid; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; tin(ll) chloride; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/ja9611093

Reference yield:

: 184178-66-3
2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

: 183954-70-3
(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: NaOMe, MeOH / CHCl₃ / 1.5 h / Ambient temperature

2: DL-camphorsulfonic acid / 1 h / Ambient temperature

3: NaH / 1.) DMF, RT, 17 h, 2.) DMF, from RT to 70 deg C, 2 h

4: 88 percent / 70percent aq. AcOH / 3 h / 60 °C

5: 1.) dibutyltin oxide, 2.) n-Bu₄NI / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 1 h

With methanol; camphor-10-sulfonic acid; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; In chloroform;
DOI:10.1021/ja9611093

Reference yield:

: β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

: 183954-70-3
(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: DL-camphorsulfonic acid / 1 h / Ambient temperature

2: NaH / 1.) DMF, RT, 17 h, 2.) DMF, from RT to 70 deg C, 2 h

3: 88 percent / 70percent aq. AcOH / 3 h / 60 °C

4: 1.) dibutyltin oxide, 2.) n-Bu₄NI / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 1 h

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid;
DOI:10.1021/ja9611093