(1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol

Base Information

• Chemical Name: (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol
• CAS No.: 220172-60-1
• Molecular Formula: C₄₇H₅₈O₁₂
• Molecular Weight: 814.97
• Mol file: 220172-60-1.mol

Synonyms:

Chemical Property of (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol

There total 8 articles about (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol 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: 70.0%

(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] (220172-59-8) → (1R,2S,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol + (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol (220172-60-1)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; water; In tetrahydrofuran; toluene; tert-butyl alcohol;

DOI:10.1039/a807190j

Reference yield:

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) → (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol (220172-60-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / benzene / Ambient temperature

2: 95 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

3: 95 percent / NaH / dimethylformamide / 1.) 30 min, 2.) r.t., 3 h

4: 70 percent / NMO, OsO₄, H₂O / tetrahydrofuran; 2-methyl-propan-2-ol; toluene

With osmium(VIII) oxide; N-methyl-2-indolinone; zinc(II) tetrahydroborate; water; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1039/a807190j

Reference yield:

benzyl bromide (100-39-0) → (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol (220172-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaH / dimethylformamide / 1.) 30 min, 2.) r.t., 3 h

2: 70 percent / NMO, OsO₄, H₂O / tetrahydrofuran; 2-methyl-propan-2-ol; toluene

With osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1039/a807190j

upstream raw materials:

(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

benzyl bromide

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosiduronyl)-(triphenylphosphoranylidene)methane

Downstream raw materials:

methyl 2,3,4,6,7,8-hexa-O-benzyl-9,10:11,12-di-O-isopropylidene-α-L-erythro-L-manno-D-gluco-1,5-pyranoside

(2R,3R,4S,5S,6R,7R)-5,6,7-Tris-benzyloxy-7-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-heptane-1,2,3,4-tetraol

(2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-((1R,2R,3S,4S,5R,6R)-1,2,3,4,5,6,7-heptakis-benzyloxy-heptyl)-6-methoxy-tetrahydro-pyran